Water → 3-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

Participants

Reaction Steps

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (Intermediate AA) (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15 g) were treated with a solution of 18 mL hydrazine hydrate in 25 mL ethanol and heated on the steambath for 1 hour, 15 mL ethanol added followed 10 mL water. The precipitated solid was collected and washed with 4:1 ethanol:water then dried in air giving 3-amino-4-Cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid 30.0 g (80%) m.p. 187-188.5° C. 1H NMR (DMSO-d6, 400 MHz) 12.11 (broad s, 1H), 7.80 (d, 2H), 7.42 (m, 2H), 7.18 (m, 1H), 7.09 (m, 4H), 6.47 (broad s, 2H). Calculated for C16H12N4O C, 69.6; H, 4.3; N, 20.3; Found C, 69.5; H, 4.4; N, 20.2.

Provenance & Evidence