Hydrochloric Acid → N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Participants

Reaction Steps

To a solution of N-cyclopropyl-3-(7-methoxy-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-4-methylbenzamide (1 g) in Methanol (20 ml) and methylene chloride (45 ml) under an atmosphere of argon was added NaBH4 (114 mg) portionwise and the reaction stirred at room temperature for 17 hours. Concentrated hydrochloric acid (0.2 ml) was added and the reaction stirred for a further 4 hours. The reaction mixture was concentrated and the resultant solid triturated with ethyl acetate and air dried to yield N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a white solid (849 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.86 (m, 1H), 3.39 (s, 3H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.50 (d, 1H), 7.67 (s, 1H), 7.71 (d, 1H), 7.89 (d, 1H), 8.44 (d, 1H); Mass Spectrum: M+H+ 349.

Provenance & Evidence