Methylamine → N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine

Participants

Reaction Conditions

Reaction Steps

Methylamine (available as a 40% solution in water, 21 mL, 0.25 mol) was added to a suspension of 6-benzyloxy-4-chloro-3-nitroquinoline (13.74 g, 43.65 mmol) in distilled water (300 mL), and the reaction was stirred at 100° C. for 1.5 hours. The reaction was allowed to cool to ambient temperature and stirred for three hours. A precipitate formed, which was isolated by filtration, washed with distilled water (3×), and recrystallized from 2-propanol (44.2 mL/g). The crystals were isolated by filtration and washed with cold hexanes (2×100 mL) to provide 11.36 g of N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine as orange crystals.

Provenance & Evidence