Yield:-

Reaction Conditions:

with hydrogen;dimethyl amine in ethanol;water;

Steps:

6 EXAMPLE 6

A solution of N-(2-nitrophenyl)-2-chloroacetamide (4.29 g) in ethanol (80 ml) containing platinum oxide catalyst (0.15 g) was shaken in an atmosphere of hydrogen, at atmospheric pressure and laboratory temperature, until 1.5 litres of hydrogen had been absorbed. The mixture was filtered. The filtrate was evaporated under reduced pressure and the residual solid triturated with water. The solid obtained, m.p. 79°-85° C., was filtered off and dissolved in ethanol. A solution of dimethylamine in ethanol (20% w/w; 10 ml) was added and the mixture heated under reflux for 2 hours. The ethanol was then evaporated under reduced pressure and water (20 ml) added to the residue. The mixture obtained was extracted with diethyl ether (3 * 50 ml) and the ethereal extracts dried over magnesium sulphate and evaporated to dryness. The residual solid was recrystallized twice from cyclohexane to give N-(2-aminophenyl)-2-dimethylaminoacetamide, m.p. 119°-121° C.

References:

US4005217,1977,A