Diethyl Ether → HCID 13145269, compound

Participants

Reaction Steps

To a stirred solution of 7.4 g. (50 mmoles) of 2-dimethylaminoisonicotinonitrile in 150 ml. of diethyl ether was added dropwise 33 ml. (100 mmoles) of a 3 M solution of methyl magnesium bromide under a nitrogen atmosphere. On completion, the reaction was allowed to stir at room temperature for 16 hours, and was then quenched by the careful addition of 80 ml. of 2 N hydrochloric acid. The aqueous phase was separated and the organic phase extracted further with 2 N hydrochloric acid (2×10 ml.). The combined acid extracts were neutralized with solid sodium carbonate and extracted with chloroform (5×50 ml.). The combined chloroform extracts were dried and concentrated to a brown oil. Distillation of the residue gave 5.0 g. (61%) of the product as an oil (b.p. 110° C./1 torr). On standing the oil crystallized, m.p. 37°-42° C.

Provenance & Evidence