Category: 20028-53-9

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives, published in 2020-06-05, which mentions a compound: 20028-53-9, mainly applied to arylazo benzazepinecarboxylate diastereoselective preparation; binaphthylphosphoric acid catalyst tandem cyclocondensation aminobenzaldehyde hydrazone unsaturated ketoester, Quality Control of 2-Amino-5-chlorobenzaldehyde.

In the presence of racemic 1,1′-binaphthalene-2,2′-diyl phosphoric acid, 2-aminobenzaldehyde aryl hydrazones 5-R1-2H2NC6H3CH:NNHR2 (R1 = H, Cl; R2 = Ph, 4-MeOC6H4, 2,5-Me2C6H3, 4-FC6H4, 4-BrC6H4) underwent tandem cyclocondensation reactions with (E)-γ-aryl-β,γ-unsaturated-α-keto esters (E)-RCH:CHCOCO2R3 (R = Ph, 4-MeC6H4, 4-BrC6H4, 4-ClC6H4, 3-ClC6H4; R3 = Me, Et, i-Pr, t-Bu) to yield arylazodihydrobenzazepinecarboxylates I (R = Ph, 4-MeC6H4, 4-BrC6H4, 4-ClC6H4, 3-ClC6H4; R1 = H, Cl; R2 = Ph, 4-MeOC6H4, 2,5-Me2C6H3, 4-FC6H4, 4-BrC6H4; R3 = Me, Et, i-Pr, t-Bu) in 89-99% yields and in >19:1 dr.

This compound(2-Amino-5-chlorobenzaldehyde)Quality Control of 2-Amino-5-chlorobenzaldehyde was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, ACS Combinatorial Science called Cyanoacetamides (IV): Versatile One-Pot Route to 2-Aminoquinoline-3-carboxamides, Author is Wang, Kan; Herdtweck, Eberhardt; Domling, Alexander, which mentions a compound: 20028-53-9, SMILESS is NC1=CC=C(Cl)C=C1C=O, Molecular C7H6ClNO, SDS of cas: 20028-53-9.

Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives

《Cyanoacetamides (IV): Versatile One-Pot Route to 2-Aminoquinoline-3-carboxamides》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(2-Amino-5-chlorobenzaldehyde)SDS of cas: 20028-53-9.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Park, Kwanghee Koh; Jung, Jin Young researched the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9 ).Product Details of 20028-53-9.They published the article 《Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes》 about this compound( cas:20028-53-9 ) in Heterocycles. Keywords: quinolinone preparation; carboxamidobenzaldehyde preparation intramol cyclocondensation; aminobenzaldehyde acyl chloride amidation. We’ll tell you more about this compound (cas:20028-53-9).

2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (I) with overall yields of 71-90 %. Subsequent reaction with base provided 3-substituted quinolin-2(1H)-ones with 63-97 % yields. Treatment of I with MeI and base gave 3-substituted 1-methylquinolin-2(1H)-ones with 82-95 % yields, whereas the treatment with Me2CHI gave 3-substituted 1-isopropylquinolin-2(1H)-ones with 7-42 % yields.

《Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(2-Amino-5-chlorobenzaldehyde)Product Details of 20028-53-9.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Zhao, Dan; Shen, Qi; Zhou, Yu-Ren; Li, Jian-Xin published an article about the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9,SMILESS:NC1=CC=C(Cl)C=C1C=O ).Reference of 2-Amino-5-chlorobenzaldehyde. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20028-53-9) through the article.

A facile alkenylation of quinazolines with unactivated terminal alkynes has been achieved in the presence of KOtBu without the aid of any transition metal catalysts. The reaction is carried out under very mild conditions and shows a high stereoselectivity. E.g., in presence of KOtBu in THF, alkenylation of quinazoline derivative (I) with PhCCH gave 89% (E)-II. A possible radical-based mechanism is also explored.

《KOtBu-mediated stereoselective addition of quinazolines to alkynes under mild conditions》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(2-Amino-5-chlorobenzaldehyde)Reference of 2-Amino-5-chlorobenzaldehyde.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Kiran, B. M.; Mahadevan, K. M. published an article about the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9,SMILESS:NC1=CC=C(Cl)C=C1C=O ).Computed Properties of C7H6ClNO. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20028-53-9) through the article.

The easy and rapid synthetic procedure for the synthesis of substituted 3-cyanoquinoline derivatives using available laboratory reagents is reported. Vilsmeier-Haack reaction is employed to the p-substituted aniline to yield formyl aniline. These on reaction with Et cyanoacetate and with malononitrile in presence catalyst results in to 3-substituted quinolines.

《Rediscovered synthesis of 3-cyanoquinoline derivatives》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(2-Amino-5-chlorobenzaldehyde)Computed Properties of C7H6ClNO.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Chlorine-Influenced Changes in the Molecular Inclusion and Packing Properties of a Diquinoline Host, published in 2007-01-31, which mentions a compound: 20028-53-9, Name is 2-Amino-5-chlorobenzaldehyde, Molecular C7H6ClNO, Recommanded Product: 2-Amino-5-chlorobenzaldehyde.

Chloro-substituted diquinoline dibromide 6 is a versatile host mol. that includes guest mols. of different functionality in several different ways. The crystal structures of 6 and its lattice inclusion compounds with carbon disulfide, dichloromethane, acetone, chloroform, benzene, and toluene are reported and analyzed in crystal engineering terms. Also described is the quinolinium inclusion compound (11)·(acetophenone). The inclusion properties of 6, and the ways that it achieves these, are very different from those of its non-chlorinated parent, 4. Different types of aromatic interfacial packing are discussed. There is far greater dependence on these types of interactions and a complete absence of the aromatic edge-edge C-H···N dimer motif in the crystal structures of 6.

Different reactions of this compound(2-Amino-5-chlorobenzaldehyde)Recommanded Product: 2-Amino-5-chlorobenzaldehyde require different conditions, so the reaction conditions are very important.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Name: 2-Amino-5-chlorobenzaldehyde. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about PPTS-Catalyzed Bicyclization Reaction of 2-Isocyanobenzaldehydes with Various Amines: Synthesis of Diverse Fused Quinazolines. Author is Meng, Xiang-He; Wu, Dan-Ni; Zhang, Yu-Jia; Zhao, Yu-Long.

A PPTS (pyridinium p-toluenesulfonate)-catalyzed bicyclization reaction of 2-isocyanobenzaldehydes 2-NC-4-R-5-R1C6H2CHO (R = H, Br, OMe; R1 = H, Cl, F, OMe) as 1,5-dielectrophiles with various amines R2NH2 (R2 = 3-hydroxypropyl, 2-amino-4,5-difluorophenyl, 2-(1H-pyrrol-1-yl)benzen-1-yl, etc.) has been developed. The reaction not only provides a simple and efficient strategy for the assembly of structurally diverse fused quinazoline derivatives e.g., I from readily available substrates under metal-free and mild conditions in a single step with only water and hydrogen as the byproducts, but also opens the way to the application of o-formyl arylisocyanides in the synthesis of nitrogen-containing heterocycles e.g., I.

Different reactions of this compound(2-Amino-5-chlorobenzaldehyde)Name: 2-Amino-5-chlorobenzaldehyde require different conditions, so the reaction conditions are very important.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Reference of 2-Amino-5-chlorobenzaldehyde. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Heterogeneous synergistic catalysis for promoting Aza-Michael-Henry tandem reaction for the synthesis of chiral 3-nitro-1,2-dihydroquinoline. Author is An, Zhe; Chen, Lifeng; Jiang, Yitao; He, Jing.

Heterogeneous synergistic catalysis by SBA-15 immobilized chiral amines catalysts has promoted efficient aza-Michael-Henry tandem reaction for the synthesis of chiral 3-nitro-1,2- dihydroquinolines (S)-I (R = Ph, 2,3-dimethoxyphenyl, 3,4-dichlorophenyl, etc.; R1 = H, 8-MeO, 6-Cl, 6,8-Br2). Final products in the asym. aza-Michael-Henry cascade reactions between 2-aminobenzaldehydes R2-2-H2NC6H3CHO (R2 = H, 3-MeO, 5-Cl, 3,5-Br2) and β-nitrostyrenes RCH=CHNO2 were afforded in a yield of 85% and an enantiomeric excess (ee) value of 98% on (S)-(-)-2-aminomethyl-1-ethylpyrrolidine immobilized SBA-15. SBA-15-AEP catalyst has been also extended to the asym. aza-Michael-Henry cascade reaction of substituted 2-aminobenzaldehydes and substituted nitroolefins. The heterogeneous synergistic mechanism for both tertiary amine and secondary amine immobilized mesoporous has been proposed in detail including the geometrical constraints in the ee promotion.

The article 《Heterogeneous synergistic catalysis for promoting Aza-Michael-Henry tandem reaction for the synthesis of chiral 3-nitro-1,2-dihydroquinoline》 also mentions many details about this compound(20028-53-9)Reference of 2-Amino-5-chlorobenzaldehyde, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

SDS of cas: 20028-53-9. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Yb(OTf)3-Mediated Annulation of Cyclopropane-1,1-dicarbonitriles with 2-Aminobenzaldehydes for Synthesis of Polysubstituted Quinolines. Author is Wan, Xinyi; Wang, Shan; Wu, Chengjun; Gan, Jianbo; Wang, Cunde.

A Yb(OTf)3-mediated annulation of cyclopropane-1,1-dicarbonitriles and 2-aminobenzaldehydes for the synthesis of polysubstituted quinolines in generally good yields was investigated. In the cascade reaction, the protocol includes ring opening, intermol. nucleophilic addition, intramol. nucleophilic addition, and de-malononitrile aromatization, in which the malononitrile group served as a deciduous directing group mediated by Yb(OTf)3.

The article 《Yb(OTf)3-Mediated Annulation of Cyclopropane-1,1-dicarbonitriles with 2-Aminobenzaldehydes for Synthesis of Polysubstituted Quinolines》 also mentions many details about this compound(20028-53-9)SDS of cas: 20028-53-9, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》. Authors are Baumgarten, Henry E.; Pedersen, Donald L.; Hunt, Mack W..The article about the compound:2-Amino-5-chlorobenzaldehydecas:20028-53-9,SMILESS:NC1=CC=C(Cl)C=C1C=O).Reference of 2-Amino-5-chlorobenzaldehyde. Through the article, more information about this compound (cas:20028-53-9) is conveyed.

cf. C.A. 50, 8672d. Crude, moist 4,2-Cl(H2N)C6H3CHO (7 g.), 2.9 g. NaNO2, and 75 g. crushed ice slurried in a Waring blender, treated with 9 cc. concentrated HCl and 50 g. crushed ice in 1 portion, blended 5 min. while adding periodically crushed ice, 4.3 cc. MeNO2 in 5 cc. EtOH added slowly with stirring to 5.7 g. KOH in 3.5 l. iced H2O, the solution treated with 3.3 g. NaOAc, the diazonium salt solution added slowly, the mixture allowed to stand 20 min. and filtered, the residue blended about 5-10 min. with 1.3 g. KOH in 50 cc. H2O, the mixture poured into a beaker, allowed to stand 2.5 hrs., and filtered, and the residue dried overnight (1.51 g.) and recrystallized from Me2CO or EtOAc yielded 1.1 g. 7-chloro-3-nitrocinnoline (I), yellow needles, m. 165.6-66° (all m.ps. are corrected). A similar run with a 4-fold larger amount of each reagent was carried out, the resulting yellow solid blended about 10 min. with 5.2 g. KOH in 200 cc. H2O, kept 2.5 hrs., and filtered, the brown residue refluxed 2 hrs. with 300 cc. Me2CO and filtered, and the filtrate treated with C, concentrated to about 75 cc., and cooled, giving 5.5-14.0 g. 5,2-Cl(AcCH:CH)C6H3NHN:CHNO2, yellow-orange needles, m. 234-5° (Me2CO). 5,2-Cl(O2N)C6H3CHO (15.6 g.) in 360 cc. hot EtOH added to 180 g. FeSO4.7H2O in 600 cc. H2O at 90°, the mixture treated slowly during 10 min. with 600 cc. concentrated NH4OH and steam-distilled, the 1st 300-500 cc. distillate discarded, and the following 2 l. distillate cooled to 5°, saturated with NaCl, and filtered yielded 6.5-7.0 g. crude 5,2-Cl(H2N)C6H3CHO (II), m. 73.5-4.5°. Crude moist II (7.0 g.) was converted as described for the preparation of I to 5.1 g. (crude) 6-Cl isomer of I, yellow plates, m. 227-8° (EtOAc). 6-Aminopiperonal (9.0 g.) was converted in the usual manner to nitroformaldehyde 4,5-methylenedioxy-2-formylphenylhydrazone and this to 1.96 g. (crude) 6,7-methylenedioxy-3-nitrocinnoline, cream-colored needles, m. 255-310° (indefinite). 3-Nitrocinnoline (13.8 g.) in 110 cc. AcOH and 55 cc. H2O treated during about 5 min. with 11 g. Fe powder, refluxed 1 hr., poured into 300 g. cold 33% aqueous KOH, kept overnight, and filtered through Celite, the filter cake washed with H2O, suspended in 150 cc. absolute EtOH, heated to boiling, filtered, and again extracted with 150 cc. and 100 cc. absolute EtOH, the combined filtrates evaporated, and the residue recrystallized from 250 cc. C6H6 gave 8.0 g. 3-aminocinnoline (III), m. 165-6°; 2nd crop, 1.1 g. I (3.0 g.) reduced similarly gave 2.2 g. 7-Cl derivative of III, bright yellow plates, m. 202° (decomposition). II (3.0 g.) gave similarly 1.91 g. 6-Cl derivative of III, bright yellow needles, m. 215° (decomposition). ο-O2NC6H4CHO (IV) (10 g.) in 50 cc. absolute MeOH treated with 2 drops concentrated HCl and 0.75 g. CaCl2, the mixture kept 6 days in a desiccator over CaCl2, filtered, neutralized with NaOMe in MeOH, and evaporated, and the oily residue distilled gave 11.4 g. ο-O2NC6H4CH(OMe)2 (V), b27 146-9°, n25D 1.5265. IV (100 g.) in 750 cc. C6H6 and 50 cc. absolute MeOH refluxed 28 hrs. with 2 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removing 500 cc. distillate, neutralized with NaOMe, and worked up in the usual manner yielded 116 g. V. IV (15 g.) in 250 cc. C6H6 and 35 cc. absolute MeOH refluxed 35 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. V. IV (10 g.) in 250 cc. C6H6 and 25 cc. (CH2OH)2 refluxed 30 hrs. with 0.25 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removal of about 150 cc. distillate, basified with NaOMe to litmus, and fractionated gave 10.3 g. ethylene acetal (VI) of IV, pale yellow oil, b0.7 120.7°, n20D 1.5487. IV (15 g.) in 250 cc. C6H6 and 10 cc. (CH2OH)2, refluxed 30 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. VI, b0.7 120°. V (5.0 g.), 100 cc. absolute MeOH, and about 1 g. Raney Ni hydrogenated about 1 hr. at 45 lb., filtered, slurried in a Waring blender with 50 cc. H2O, 3.5 g. NaNO2, and 300 g. crushed ice, treated with 25 cc. 6N HCl, and slurried again 20 min. while adding periodically crushed ice, the mixture added dropwise with stirring during 20 min. to a solution of 3.0 g. MeNO2, 10 cc. EtOH, and 5.7 g. KOH in 400 cc. H2O, and the precipitate recrystallized from 1:3 Me2CO-H2O gave 4.3 g. ο-O2NCH:NNHC6H4CH(OMe)2 (VII), bright orange needles, m. 80-1°. VI (4.3 g.), 50 cc. absolute MeOH, and about 0.5 g. Raney Ni hydrogenated, filtered, diazotized in a blender with 3 g. NaNO2, 100 cc. H2O, 300 g. ice, and 22 cc. 6N HCl, added to a solution of 4 g. MeNO2, 10 cc. EtOH, and 7.5 g. KOH in 400 cc. iced H2O, adjusted with cold 1% HCl to pH 3, stirred 20 min. at 5°, and filtered gave 2.5 g. ethylene acetal (VIII) of ο-O2NCH:NNHC6H4CHO (IX), golden yellow plates, m. 83.6-85° (aqueous Me2CO); the filtrate warmed to room temperature and extracted with Et2O, and the extract evaporated gave 1.8 g. IX, m. 156-8°. VII (0.87 g.) added at 95° to 3 cc. concentrated HCl in 200 cc. H2O in a Waring blender, the solution blended 0.5 hr., cooled to 10°, and extracted with Et2O, and the extract worked up gave 0.66 g. IX, m. 157-8°. VIII (0.65 g.) hydrolyzed similarly with 2 cc. concentrated HCl in 150 cc. hot H2O yielded 0.49 g. IX. IX (2.0 g.) in 300 cc. tetrahydrofuran circulated 18 hrs. at 55° through 6 g. dry Amberlite IRA-400, filtered, and evaporated gave 1.0 g. 3-nitrocinnoline, m. 204-5° (aqueous Me2CO).

The article 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》 also mentions many details about this compound(20028-53-9)Reference of 2-Amino-5-chlorobenzaldehyde, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem