Malononitrile → HCID 10203487, compound

Participants

Reaction Steps

To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol (2 ml) was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min, then refluxed for 1 h, and cooled to room temperature. To the mixture was added piperidine (0.1 ml, 1 mmol) and 5-hydroxyquinoline (145 mg, 1 mmol). The mixture was refluxed for 1 h, and the solvent was evaporated. The residue was purified by chromatography on silica gel (EtOAc/hexane, 1:2), yielding the title compound (50 mg, 11%). 1H NMR (CDCl3): 8.95 (s, 1H), 8.50 (d, J=9.0, 1H), 7.82 (d, J=9.0, 1H), 7.50 (brs, 1H), 7.30 (s, 1H), 6.92 (s, 1H), 6.76 (s, 1H), 4.82 (brs, 3H), 3.84 (s, 6H).

Provenance & Evidence