Dimethylformamide dimethyl acetal → HCID 178488756, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile (5.0 g, 23 mmol) in DMF (12 mL) was added dimethylformamide-dimethylacetal (DMF-DMA, 13.5 mL, 101 mmol) and the solution heated at 122° C. overnight. Concentration on a rotary evaporator under high vacuum gave an orange-red solid. This solid was dissolved in EtOH (100 mL) and excess ammonium acetate was added and the reaction mixture was heated at 85° C. for 1 h. The reaction mixture was allowed to cool to room temperature (r.t.) for 1 h then the solids were collected by filtration and washed with EtOH (cold) to give 5-(3,4-dimethoxyphenyl)-4-hydroxynicotinonitrile (4.1 g, 69%) as a brown solid. The filtrate was concentrated on a rotary evaporator and the residue purified on silica gel with 0-25% MeOH in CH2Cl2 to give an additional amount of 5-(3,4-dimethoxyphenyl)-4-hydroxynicotinonitrile.

Provenance & Evidence