Hydrochloric Acid → Ethyl 2-chloro-2-[2-(2,4-dichlorophenyl)hydrazinylidene]acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4-dichloroaniline (1 g, 6.17 mmol) and concentrated hydrochloric acid (1.5 ml) in ice (1.5 ml) a solution of NaNO2 (0.460 mg, 6.68 mmol) in water (0.8 ml) is slowly added and the mixture is stirred for 1 h at 0-5° C. Then, this solution is added over a cold mixture of NaOAc (1.64 g, 19.6 mmol), ethanol (26 ml) and ethyl-2-chloro-3-oxobutanoate (1.0 g, 6.06 mmol) and let stirring for 1 hour until the formed precipitate is collected by filtration, washed with ethanol and dichloromethane and dried in vacuo to give the yellow solid ethyl 2-chloro-2-(2-(2,4-dichlorophenyl)hydrazono)acetate (70-80% yield), which is used in the next step without any further purification.

Provenance & Evidence