Dimethyl Sulfide → 6,7-Dihydro-5H-quinoline-8-one

HRID 18247Notes

Reaction equation

HRID 18247 reaction equation
C(=[C:8]1[C:17]2[N:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[O:18]=[O+][O-].CSC>C(Cl)Cl>[N:16]1[C:17]2[C:8](=[O:18])[CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 540746508-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

Product 1

HCID 117447776,7-Dihydro-5H-quinoline-8-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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)+.

Workup

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

Sources & evidence

ORD record
ord-a507620eadea444ba64e00db97327bb4
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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