Dimethylformamide → HCID 66664935, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(7-bromo-3-methoxy-naphthalen-2-yl)-acetamide (1.2 g, 4.0 mmol) in a previously degassed mixture of water and N,N-dimethylformamide (3/1, 40 mL) was added zinc cyanide (0.28 g, 2.4 mmol) followed by tris(dibenzylideneacetone)dipalladium(0) (0.18 g, 0.22 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.27 g, 0.48 mmol) and the resulting mixture was heated at 120° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed 3 times with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc) to afford 0.621 g of N-(7-cyano-3-methoxy-naphthalen-2-yl)-acetamide as a cream colored solid. MS=241 [M+H]+.

Provenance & Evidence