Water → HCID 13228733, compound

HRID 1761322Notes

Reaction equation

HRID 1761322 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].O>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:6][C:5]([N:9]2[C:10](=[O:19])[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:16]=3[C:17]2=[O:18])=[C:4]([F:20])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1586511H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-

Product 1

HCID 13228733HCID 13228733, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (3 g) is dissolved in dimethylformamide (100 ml), and anhydrous potassium carbonate (0.8 g) is added thereto. To the resultant mixture is added methyl bromoacetate (1.8 g), and the mixture is heated at 70°-80° C. for 3 hours. After being allowed to cool, water is added to the mixture, which is then extracted with ether, and the extract is washed with water, dried and concentrated. The residue is purified by silica gel column chromatography to give 1.3 g of 2-(4-chloro-2-fluoro-5-methoxycarbonylmethoxyphenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 1). M.P., 98°-99.5° C.

Workup

  1. temperaturethe mixture is heated at 70°-80° C. for 3 hours
  2. temperatureto cool
  3. extractionis then extracted with ether
  4. washthe extract is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b9d4e8b53224acea62216e2b6fb8892
Source dataset
uspto-grants-1989_05
Patent number
US04826533

Reaction notes

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