Methanol → HCID 86757810, compound

HRID 1700705Notes

Reaction equation

HRID 1700705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13]([NH:15][NH:16]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:12][C:11](=O)[CH2:10]1.C(=O)([O-])[O-].[K+].[K+].CO.Br[CH2:37][C:38](=O)[CH3:39]>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13]2[N:15]=[N:16][CH:37]=[C:38]([CH3:39])[C:12]=2[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 18317325HCID 18317325, compound

Product 1

HCID 86757810HCID 86757810, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-(2-chloro-5-methylphenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (2.03 g), anhydrous potassium carbonate (1.73 g) and methanol (20 ml) was stirred at room temperature for 30 minutes, and to the mixture were added 1,2-dimethoxyethane (10 ml) and bromoacetone (0.891 g). The mixture was stirred at 80° C. for 4.5 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (200 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-(2-chloro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin,-5-one (0.804 g) as brown crystals.

Workup

  1. stirringThe mixture was stirred at 80° C. for 4.5 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue were added ethyl acetate (200 ml) and water (30 ml)
  4. stirringThe mixture was shaken
  5. washthe separated upper layer was washed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-006ed620215b473bbdf21790cbd92530
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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