2-Chlorobenzaldehyde → HCID 2818274, compound

Participants

Reaction Conditions

Reaction Steps

This material was prepared in a similar manner to that described in Acta Chimica Academiae Scientiarum Hungaricae 1969, 60(1-2), 177. Thus a mixture of benzyl cyanide (40 g, 342 mmol) and polyphosphoric acid (200 g) was heated and stirred at 80° C. for 45 minutes. 2-Chlorobenzaldehyde (24 g, 171 mmol) was added with very vigorous stirring over 25 minutes. The mixture was heated to 135° C. for 31/2 h, cooled to 100° C. and poured into water (450 ml). 0.88 Ammonium hydroxide (600 ml) was added and the mixture left overnight. The precipitate was filtered off and refluxed in 5% sodium hydroxide (500 ml). The mixture was filtered hot after 2 h and the solid (30 g) chromatographed (SiO2, 200 g) using chloroform as eluent. This gave a solid that was crystallised (ethanol) to give 1-(2-chlorophenyl)-1,4-dihyroisoquinol-3-one (20.5 g, 47%) m.p. 180°-2° C.

Provenance & Evidence