Hydrochloric Acid → 4-Methoxyisonitrosoacetanilide

Participants

Reaction Conditions

Reaction Steps

Chloral hydrate (9.6 g) was dissolved in 200 mL water containing 83 g sodium sulfate. The solution was warmed to 60° C., a solution of 11.4 g hydroxylamine hydrochloride in 50 mL water was added and the mixture was held at 60° C. In a separate flask, 6.4 g 4-anisidine and 4.3 mL concentrated hydrochloric acid in 80 mL of water and was warmed to 80° C. The first solution was added to the second and the resulting mixture was refluxed for 2 minutes, cooled slowly to room temperature, and then cooled in an ice bath. The tan precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 8.6 g (85% yield) of N-(2-hydroximinoacetyl)anisidine.

Provenance & Evidence