Oxygen → HCID 178483298, compound

Participants

Reaction Steps

2-Dimethylaminomethylacrylonitrile (11.0g) was added in one portion to a solution of phenylhydrazine (10.8g) and sodium ethoxide (2.3g sodium) in ethanol (100 ml). The product was rapidly oxidised in alkaline solution to a deep purple material; contact with oxygen was prevented by vigorous boiling of the solvent during 11/2 hours reflux. After cooling, the sodium ethoxide was neutralised with sulphuric acid (50 ml 2N) and the mixture was extracted with chloroform (3 × 100 ml). Evaporation of the solvent gave a brown solid (17.8g) which was recrystallised from petroleum ether (boiling point 80°-100° C; 300 ml) to yield colourless plates (16.4g, 75%, melting point 117°-8° C).

Provenance & Evidence