Water → 5-((Diphenylmethylene)amino)nicotinaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-[(diphenylmethylene)amino]-N-methoxy-N-methylnicotinamide (Preparation 23, 7.50 g, 0.021 mol) in THF (150 mL) at −70° C. was added diisopropylaluminium hydride (42 mL, 0.042 mol, 1.0 M in THF) and the resulting mixture stirred at −70° C. for 2 hours. Water (20 mL) and ethyl acetate (100 mL) were added. The organic phase was separated, concentrated under reduced pressure and purified by silica gel column chromatography eluting with EtOAc: petroleum ether 1:10 to afford the title compound as a brown solid in 65% yield, 4 g.

Provenance & Evidence