Reaction #433641

Reaction equation

7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

sodium acetate

water

dichloromethane

→

3-acetyl-7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

Yield 79.0%

Solvents

acetic acid anhydride

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was cooled
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with a saturated solution of sodium hydrogencarbonate
4. 4
   Otherfinally, evaporated
5. 5
   OtherFor purification
6. 6
   Otherthe crude material obtained
7. 7
   Otherwas chromatographed on silica gel using a 4

Procedure

A mixture of 50 mg (0.2 mmol) of 7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one and 33 mg (0.4 mmol) of sodium acetate in 0.12 ml of acetic acid anhydride was heated to 145° C. during 4.5 hours. For the working-up, the reaction mixture was cooled and treated with water and dichloromethane. The organic layer was separated, washed with a saturated solution of sodium hydrogencarbonate, and, finally, evaporated. For purification, the crude material obtained was chromatographed on silica gel using a 4:1-mixturet of heptane and ethyl acetate as the eluent. There were obtained 45 mg (79% of theory) of 3-acetyl-7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one as a white foam; MS: m/e=344 (M+H)+.

Source