Sodium Hydroxide → 2-acetylamino-4-nitrophenyl gamma-N,N-dimethylaminopropyl ether

Participants

Reaction Conditions

Reaction Steps

35.1 g (0.15 mol) of 2-acetylamino-4-nitrophenol, in the form of the potassium salt, are introduced into 105 ml of dimethylformamide and the mixture is then heated to 60° C., whilst stirring. 25.8 g (0.21 mol) of γ-dimethylaminopropyl chloride are then added; the reaction medium is heated at 90° C. for 210 minutes and is then poured into 750 g of iced water to which 40 ml of 1 N sodium hydroxide solution have been added. The expected product is extracted with methyl isobutyl ketone. After the methyl isobutyl ketone has been driven off in vacuo, the expected product is obtained in the form of an orange oil which crystallises rapidly (melting point: 69° C.).

Provenance & Evidence