Phenylhydrazine → 2-(2-Phenylhydrazono)malonic acid

Participants

Reaction Steps

To a vigorously stirred solution of ketomalonic acid monohydrate (29.33 g) in ethanol (140 mL) and water (300 mL) at ambient temperature was added phenylhydrazine (23.3 g) dropwise over a 40 minute period. The resultant slurry was stirred overnight at ambient temperature. The solid was separated by filtration, washed sucessively with cold water (100 mL) and ethanol (25 mL) and air dried. Subsequent drying was performed at 75° C. overnight in a vacuum oven to give the title compound as a yellow solid (42.38 g). 1H (300 MHz, DMSO-d6): d 7.12(t, 1H), 7.35-7.48(m, 4H); m.p.: 155°-157° C. (dec).

Provenance & Evidence