Water → HCID 86758883, compound

Participants

Reaction Steps

3-(4-Chlorophenyl)indeno[1,2-c]pyrazol-4(1H)-one (0.68 g) was dissolved in N,N-dimethylformamide (30 ml) under nitrogen at 20° C. Sodium hydride (106 mg, of a 60% dispersion in mineral oil) was added and the mixture was stirred for 30 minutes, then iodomethane (0.38 g) was added. The mixture was stirred at 20° C. for 2 hours and then poured into water (50 ml). A yellow solid was collected by filtration and washed with petroleum ether (25 ml). The solid was dissolved in hot ethyl acetate and pre-absorbed onto silica which was applied to the top of the silica column. The mixture was separated by flash column chromatography using dichloromethane/petroleum ether/methanol (50:50:1). Fractions were collected, combined as appropriate, and evaporated to give a solid which was crystallised from ethyl acetate to give 3-(4-chlorophenyl)-1-methylindeno [1,2-c]pyrazol-4(1H-one, m.p. 219-221° C. δH[2H6] DMSO (250 MHz) 4.07 (3H, s, NMe), 7.41 (1H, t, Ar), 7.55 (4H, m, Ar), 7.65 (1H, d, Ar-8-H), 8.13 (2H, d, Ar). The structure was identified by the presence of a Nuclear Overhauser Effect.

Provenance & Evidence