Dimethylformamide → HCID 53960770, compound

Participants

Reaction Steps

A stirred solution of 100 g (0.72 mol) of 2-acetyl-5-norbornene (Aldrich Chemical Co.), 65 g (0.76 mol) of cyanoacetic acid, 2 ml of ammonium hydroxide (58%), 132 ml of dimethylformamide; and 170 ml of benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the evolution of carbon dioxide ceased (approx. 24 hr.). Upon completion the reaction was cooled and the solvent removed under reduced pressure. The residue oil was distilled under vacuum to give 36 g (31% yield) of 2-(2-cyano-1-methylethylidene)-bicyclo[2.2.1]hept-5-ene: b.p. 73°-84° C./1 mm; ir 3060, 2255, 2225, 1450, 1420, 1330, 905, 730, 715: nmr 1.2-2.2 (m), 2.7-3.4 (m), 5.0-6.1 (m, vinylic H); ms 159.

Provenance & Evidence