Hydrochloric Acid → 6-Nitro-4,8-dimethylquinaldine

반응식

[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[OH-].[Na+]>>[N+:9]([C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=1)[N:4]=[C:8]([CH3:7])[CH:2]=[C:3]2[CH3:5])([O-:11])=[O:10]

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 74412-Methyl-4-nitroaniline

HCID 14798Sodium Hydroxide

생성물 1

HCID 213229256-Nitro-4,8-dimethylquinaldine수율 78.5%

실험 절차

A mixture consisting of 608 g (4.0 moles) of 2-methyl-4-nitroaniline and 1,216 g of conc. hydrochloric acid was maintained at 90°-95° C., and with good stirring, 488 g (4.8 moles) of 2-pentanon-4-ol was added dropwise over a period of 2 hours. After the addition, the reaction was further carried out for 1 hour. After cooling, a conc. aqueous solution of 528 g of sodium hydroxide was added under ice cooling to render the reaction mixture alkaline. The alkaline reaction mixture was separated into layers, and the oily layer was distilled at 2-5 mmHg to afford 340 g (1.57 moles) of 6-nitro-4,8-dimethylquinaldine.