Ozone → HCID 10450418, compound

HRID 1534491Notes

Reaction equation

HRID 1534491 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-9e3d8b16150340609692bae2e59fb0a7
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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