Hydrochloric Acid → HCID 86743917, compound

Participants

Reaction Steps

To a solution of 2-aminobiphenyl (10.16 g) in HOAc (36 ml) was added water (18 ml) and concentrated hydrochloric acid (18 ml). The solution was cooled to -15° with stirring. To this mixture was added dropwise a solution of sodium nitrite (4.36 g) in water (18 ml), maintaining the internal temperature below -5°. The resulting clear purple solution was stirred an additional 10 min at -10°, and was then added to a solution of N-propyl-2-cyanoacetamide (Prepared according to Shulka, J. S., et al., Journal of the Indian Chemical Society, (1978) 55:281-283.) (9.08 g) in water (400 ml)/ethanol (200 ml) containing sodium acetate (80 g) which had been chilled to -4°. This mixture was stirred mechanically at 0° for 6 hours before being allowed to warm to room temperature over a 15 hr. period. The mixture was then diluted with water (600 ml) and stirred. After 51/2 hours, the precipitated solid was collected by filtration and was washed with water and hexane. There was thus obtained 19.47 grams (>100% crude yield) of title product as a 5:1 ratio of Z:E isomers, m.p. 180°-184°; 1H NMR (CHCl3 -d, characteristic peaks of Z-isomer only): 0.948 (t, 3H), 1.53 (m, 2H), 3.20 (q, 2H), 6.04 (br.t, exchangeable, 1H), 7.20-7.29 (m, 2H), 7.37-7.54 (m, 6H), 7.76 (d. 1H), 13.96 (br.s, exchangeable, 1H) ppm.

Provenance & Evidence