Reaction #50645

Reaction equation

4-chloro-3-trifluoromethylcinnamonitrile

hydroxylamine hydrochloride

sodium carbonate

→

(E)-4-chloro-3-trifluoromethylcinnamamide oxime

Yield 40.1%

Solvents

water

water

ethanol

Conditions

Workup

1. 1
   TemperatureThe mixture is heated
2. 2
   Temperatureat reflux temperature until the reaction
3. 3
   Other(24 hours)
4. 4
   Filtrationis filtered off with suction
5. 5
   Washwashed with a little water
6. 6
   Otherdried

Procedure

12.1 g (0.05 mol) of 4-chloro-3-trifluoromethylcinnamonitrile are added to a solution consisting of 7.2 g (0.10 mol) of hydroxylamine hydrochloride and 7.3 g (0.10 mol) of sodium carbonate in 100 ml of water and 100 ml of ethanol. The mixture is heated at reflux temperature until the reaction is complete (24 hours) and the whole batch is subsequently stirred into 250 ml of water. The solid material which separates off during this process is filtered off with suction, washed with a little water and dried. 5.3 g (39.3% of theory) of (E)-4-chloro-3-trifluoromethylcinnamamide oxime are obtained.

Source