Potassium bisulfate → HCID 21496698, compound

HRID 1730246Notes

Reaction equation

HRID 1730246 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](O)([CH3:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:19])=[C:4]([F:20])[CH:3]=1.S(=O)(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[CH2:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 21496693HCID 21496693, compound

Product 1

HCID 21496698HCID 21496698, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Twenty-one parts of 2-(4-chloro-2-fluorophenyl)-2,-3,4,5,6,7-hexahydro-3-hydroxy-3-methyl-1H-isoindol-1-one and one part of potassium bisulfate were heated with occasional stirring in an oil bath at 160°-170° for 15 minutes. The melt was poured into 200 parts of chloroform and washed successively with 100 parts of water, 50 parts of 10% aqueous sodium hydroxide and 100 parts of saturated aqueous sodium chloride solution. After drying the organic phase with anhydrous sodium sulfate, the solvent was evaporated at 300 mm. Hg at 50°. The residue was crystallized from 100 parts of absolute ethanol to yield 10.1 parts of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-methylene-1H-isoindol-1-one melting at 84.0°-85.5°.

Workup

  1. washwashed successively with 100 parts of water, 50 parts of 10% aqueous sodium hydroxide and 100 parts of saturated aqueous sodium chloride solution
  2. dry with materialAfter drying the organic phase with anhydrous sodium sulfate
  3. customthe solvent was evaporated at 300 mm. Hg at 50°
  4. customThe residue was crystallized from 100 parts of absolute ethanol

Sources & evidence

ORD record
ord-a0630b8387cb4c74b77251f01f2b5a27
Source dataset
uspto-grants-1976_11
Patent number
US03992189

Reaction notes

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