Methanol → HCID 18317494, compound

HRID 1700707Notes

Reaction equation

HRID 1700707 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F: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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F: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 18317652HCID 18317652, compound

Product 1

HCID 18317494HCID 18317494, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 5-(5-chloro-2-fluorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (2.0 g), anhydrous potassium carbonate (1.68 g), methanol (20 ml) and 1,2-dimethoxyethane (10 ml) was added under ice-cooling 1-bromopropan-2-one (0.87 g), and the mixture was stirred for 2 hours at room temperature, and then for 6 hours at 80° C. Under reduced pressure, the solvent was evaporated, and to the residue was 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-chloro-2-fluorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (0.338 g) as yellowish brown crystals.

Workup

  1. additionwas added under ice-
  2. waitfor 6 hours at 80° C
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue was 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-4a12996a4ee84fab8b2c40aaaa6f142b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…