Diisopropylethylamine → 2-(3-Amino-2-methoxyprop-1-ylamino)-4-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-methoxyquinoline (1.75 g, 0.00903 mol), 2-methoxy-1,3-propanediamine, bis(trifluoroacetate) (6.00 g, 0.0181 mol) and N,N′-diisopropylethylamine (20 ml) was stirred for 18 h at 110° C. in a sealed reaction tube. After cooling the two phase mixture was diluted in methanol, concentrated onto silica, and then purified by silica gel chromatography (100% dichloromethane, 5%, 10% then 20% (10% 880 aqueous ammonia in methanol) in dichloromethane) to give the title compound as a yellow oil (0.86g, 36%). δH (CD3OD) 3.26-3.56 (4H, m, 2CH2), 3.46 (3H, s, CHOCH3), 3.40-3.60 (1H, m, CHOCH3), 4.02 (3H, s, COCH3), 6.10 (1H, s, 3-H), 7.00-7.81 (4H, m, ArH). MS (ES+) 262 (M+H).

Provenance & Evidence