Ozone → HCID 10450418, compound

HRID 1647476Notes

Reaction equation

HRID 1647476 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:25]=C)(=[O:5])[CH2:2][CH2:3][CH3:4].[O:27]=[O+][O-]>CO.ClCCl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:25]=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 24823OzoneHCID 10020530HCID 10020530, compound

Product 1

HCID 10450418HCID 10450418, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-vinylquinoline (5.0 g, 14.4 mmol) was stirred at -60° C. in a mixture of methanol (100 ml) and dichloromethane (200 ml) and ozone bubbled through for 15 minutes. The ozone mixture was flushed out of the reaction with nitrogen. Dimethylsulphide (2.5 ml) was added and the mixture allowed to warm to room temperature. The solvent was evaporated and the residue was chromatographed (silica gel, methanol 1% in dichloromethane) to afford 3-butyryl-4-(4-hydroxy-2-methylphenylamino)quinoline-8-carbaldehyde (2.1 g, 42%) as an oil.

Workup

  1. custombubbled through for 15 minutes
  2. customThe ozone mixture was flushed out of the reaction with nitrogen
  3. additionDimethylsulphide (2.5 ml) was added
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed (silica gel, methanol 1% in dichloromethane)

Sources & evidence

ORD record
ord-48c91957fe0b438d86fb3567e280fdea
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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