2-Chloroaniline → ethyl 4-(4-chlorophenyl)-2-[(2-chlorophenyl)hydrazinylidene]-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (3.4 g, 50.4 mmol) in water (15 ml) was added dropwise over an hour period to a cooled (0° C.), stirred solution of 2-chloroaniline (6.4 g, 50.4 mmol) in acetic acid (50 ml)/water (7 ml). Then a solution of 4-(4-chloro-phenyl)-3-oxo-butyric acid ethyl ester (10 g, 42 mmol) in acetic acid (30 ml) was added dropwise over a 30-minutes period to produce an orange slurry (20 ml of water added to aid stirring). After an additional hour, the mixture was filtered, solids washed with water and air-dried. Solids slurried in ethanol (75 ml) for 30 minutes, filtered, solids washed with methanol and dried in vacuo to afford the title compound (I-2b) as an orange solid, 11.0 g.

Provenance & Evidence