Reaction #46525

Reaction equation

Dimethyl sulfide

8-benzylidene-5,6,7,8-tetrahydro-quinoline

ozone

→

title compound

Yield 79.0%

6,7-Dihydro-5H-quinolin-8-one

Yield 79.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated in vacuo
2. 2
   Otherthe residue was purified by flash chromatography on silica gel (EtOAc)

Procedure

A solution of 8-benzylidene-5,6,7,8-tetrahydro-quinoline (4.30 g, 19.4 mmole) in CH2Cl2 (150 mL) was reacted with ozone at −78° C. for 30 minutes. Dimethyl sulfide (5 mL) was added, and the reaction was warmed to RT and stirred overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (EtOAc). The title compound (2.20 g, 79%) was obtained as an off-white solid after drying in vacuo: MS (ES) m/e 148 (M+H)+.

Source