Malononitrile → 2-amino-3-cyano-7-ethoxy-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene

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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 3-ethoxyphenol (138 mg, 1 mmol) was added and it was stirred overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel (EtOAc/Hexane, 1:2) to yield the title compound. 1H NMR (CDCl3): 6.84-6.82 (m, 2H), 6.70 (s, 1H), 6.61-6.65 (m, 1H), 6.53 (s, 1H), 4.62 (m, 3H), 4.0 (q, J=6.0, 2H), 3.82 (s, 6H), 1.4 (t, J=6.0, 3H).

Provenance & Evidence