Dimethylformamide → N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (140 mg) in methylene chloride (3 ml) was added thionyl chloride (40 μl) and DMF (40 μl) and the solution heated to 40° C. for 35 minutes. The reaction mixture was cooled to room temperature and 2M ethylamine in THF (2.1 mL) was added and the reaction stirred at room temperature for 2 hours. The reaction was dissolved in 1N NaOH and washed with ethyl acetate. The aqueous layer was acidified to pH 3 and extracted with ethyl acetate (×3). The organic layers were dried (magnesium sulfate) and concentrated to yield N-ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a solid (88 mg); NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.09 (s, 3H), 3.30 (m, 2H), 6.66 (d, 1H), 7.11 (d, 1H), 7.25 (d, 1H), 7.49 (d, 1H), 7.60 (s, 1H), 7.61 (d, 1H), 7.77 (s, 1H), 7.89 (d, 1H), 8.47 (s, 1H); Mass Spectrum: M+H+ 323.

Provenance & Evidence