Sodium cyanoborohydride → N-[2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2,4-dichlorophenyl)-propan-2-one oxime (3.3 g, 15.1 mmol) in acetic acid (30 ml) was treated at 10° C. with sodium cyanoborohydride (1.90 g, 30.3 mmol) added in small portions over 10 minutes and the resulting solution was stirred at 23° C. for 5 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with water and pH was adjusted to 10 with 1M NaOH. The aqueous phase was extracted with dichloromethane (3×20 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent (100 mbar; 45° C.), 3.18 g (96.0% of theory) of N-[2-(2,4-dichlorophenyl)-1-methyl-ethyl]-hydroxylamine was obtained in form of a white solid (m.p. 83-86° C.).

Provenance & Evidence