Dimethylformamide → (E)-2-(5-methoxy-2-nitrophenyl)-N,N-dimethylethenamine

Participants

Reaction Steps

A solution of 3.0 g. of 3-methyl-4-nitroanisole, 5.1 g. of N,N-dimethylformaide dicyclohexyl acetal, and 25 ml. of N,N-dimethylformamide was heated at reflux under a nitrogen atmosphere for 40 hours and then was transferred to a Claisen flask. Vacuum distillation gave, after removal of the volatile components, 1.89 g. of a red liquid (b.p. 158°/0.04 mm.) which crystallized on scratching to give a solid, having a melting point of 61°-64°. Recrystallization from 10 ml. of ether and 7 ml. of petroleum ether gave 1.46 g (36%) of trans-β-dimethylamino-5-methoxy-2-nitrostyrene having a melting point of 67.5°-69°.

Provenance & Evidence