Ethanol → N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide

Participants

Reaction Steps

Follow the procedures essentially as described in Preparation 6, above, using acetyl chloride (26 mL, 360 mmol) and absolute ethanol (90 mL) with 3-methoxyphenylhydrazine hydrochloride (5.24 g, 30 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (5.50 g, 30 mmol). When complete, dilute the reaction with ethyl acetate (200 mL) and wash with 0.5N NaOH and sodium bicarbonate solution. Filter the solids in the organic phase, triturate in dichloromethane and filter to give 2.67 g (31%) gray solid. MS (ES): m/z 287 (M+1), 285 (M−1); 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.21 (d, 1H, J=8.4 Hz), 6.78 (s, 1H), 6.60 (d, 1H, J=8.4 Hz), 4.00 (m, 1H), 3.75 (s, 3H), 2.87 (dd, 1H, J=14.8, 5.1 Hz), 2.76 (m, 2H), 2.48-2.36 (m, 2H), 2.48-2.36 (m, 2H), 1.76 (m, 1H), 1.03 (d, 6H, J=6.6 Hz).

Provenance & Evidence