3,4-Dichlorobenzaldehyde → 2-[3-(3,4-Dichlorobenzylamino)-2-methoxyprop-1-ylamino]-1H-quinolin-4-one

Participants

Reaction Steps

A suspension of 2-(3-amino-2-methoxyprop-1-ylamino)quinolin-4-one dihydrochloride (0.15 g, 0.468 mmol), sodium acetate (0.096 g, 1.17 mmol) and 3,4-dichlorobenzaldehyde (0.082 g, 0.468 mmol) in 1% acetic acid in methanol (1.4 ml) was stirred at room temperature for 4 h. Sodium cyanoborohydride (0.059 g, 0.937mol) in methanol (1.1 ml) was added and stirring continued for 72 h. The mixture was concentrated and chromatographed (2%, 5% then 10% (10% 880 aqueous ammonia in methanol) in dichloromethane) to yield the title compound as a white solid (0.046 g, 24%). δH (CD3OD) 2.60-3.51 (5H, m, 2CH2CH, CHOCH3), 3.34 (3H, s, CHOCH3), 3.68-3.69 (2H, d, CH2Ar), 5.58 (1H, s, 3-H), 7.21-8.09 (7H, m, ArH). MS (ES+) 406 (M+).

Provenance & Evidence