Hydrochloric Acid → 3-Chloro-4-(6-hydroxyquinolin-2-yl)benzamide

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5](O)=[O:6].O=S(Cl)Cl.Cl.[NH4+:27].[OH-]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5]([NH2:27])=[O:6]

참가 물질

반응물 4

HCID 313Hydrochloric Acid

HCID 14923Ammonium Hydroxide

HCID 24386Thionyl Chloride

HCID 56960912Cavosonstat2회

생성물 1

HCID 669800833-Chloro-4-(6-hydroxyquinolin-2-yl)benzamide

반응 조건

온도: 30 °C

실험 절차

A mixture of 3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid (Compound 8, Example 8) (400 mg, 1.33 mmol) and SOCl2 (10 mL) was refluxed for 1 hour, then concentrated under reduced pressure to give crude product (400 mg) as off-white solid. To this solid was added NH4OH (10 mL) and the reaction mixture was stirred at 30° C. for 1 hour. The resulting mixture was acidified with aqueous HCl (2 M) until pH=6 and extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated to give crude product (360 mg) as a solid.