Reaction #56828

Reaction equation

Hydrogen chloride

5-chloro-2-methoxy-benzonitrile

ethanol

→

5-chloro-2-methoxy-benzimidic acid ethyl ester

Yield 56.0%

Conditions

Workup

1. 1
   Concentrationthe mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was treated with ethyl acetate (25 ml)
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   FiltrationFiltration

Procedure

Hydrogen chloride gas (˜200 mmol) was passed into a solution of 5-chloro-2-methoxy-benzonitrile(1.68 g, 10.0 mmol) in ethanol (50 ml). After stirring for 48 hours, the mixture was concentrated under reduced pressure. The residue was treated with ethyl acetate (25 ml) and stirred for 1 hour. Filtration provided 5-chloro-2-methoxy-benzimidic acid ethyl ester (1.20 g, 56% yield) as a white powder.

Source