Methanol → HCID 18317394, compound

HRID 1700706Notes

Reaction equation

HRID 1700706 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:27])=[C:6]([CH:8]2[CH2:13][C:12]([NH:14][NH:15]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:11][C:10](=[O:26])[CH2:9]2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CO.Br[CH2:37][C:38](=O)[CH3:39]>COCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:27])=[C:6]([CH:8]2[CH2:13][C:12]3[N:14]=[N:15][CH:37]=[C:38]([CH3:39])[C:11]=3[C:10](=[O:26])[CH2:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 18317465HCID 18317465, compound

Product 1

HCID 18317394HCID 18317394, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 5-(5-fluoro-2-methylphenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.63 g), anhydrous potassium carbonate (1.45 g), methanol (20 ml) and 1,2-dimethoxyethane (10 ml) was added under ice-cooling 1-bromopropan-2-one (0.75 g), and the mixture was stirred at room temperature for 2 hours and then at 80° C. for 5 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (70 ml) and water (30 ml). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (0.265 g) as yellowish brown crystals.

Workup

  1. additionwas added under ice-
  2. waitat 80° C. for 5 hours
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue were added ethyl acetate (70 ml) and water (30 ml)
  5. stirringThe mixture was shaken
  6. washthe separated upper layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-0dec3ca5c3e3484b940f93ef1ad58880
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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