Hydrochloric Acid → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 21465

Reaction equation

HRID 21465 reaction equation
C1(C)C=CC(S(O[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)(=O)=O)=CC=1.[F:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([OH:25])=[CH:20][C:19]=1[N:26]1[C:30](=[O:31])[C:29]2[CH2:32][CH2:33][CH2:34][CH2:35][C:28]=2[C:27]1=[O:36].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[F:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:20][C:19]=1[N:26]1[C:30](=[O:31])[C:29]2[CH2:32][CH2:33][CH2:34][CH2:35][C:28]=2[C:27]1=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1586511H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate

Product 1

HCID 15279390N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimideYield 31.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopentyl p-toluenesulfonate (1.90 g, 8.11 mmol) was added to a solution of N-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (2.0 g, 6.76 mmol) and potassium carbonate (0.60 g, 4.34 mmol) in acetonitrile (50 ml), followed by stirring for 2 hours at 80° C. After completion of the reaction, 1N hydrochloric acid (20 ml) was added to the resulting reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×3 times). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Ethanol (5 ml) was added to the resulting pale yellow oily substance, and the precipitated N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a white solid (0.77 g, 2.12 mmol, 31.4% yield) was isolated by filtration. The spectral data and the like are as described in Example 1.

Workup

  1. additionwas added to the resulting reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (20 ml×3 times)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionEthanol (5 ml) was added to the resulting pale yellow oily substance

Sources & evidence

ORD record
ord-c40429fedc8b48e5945f7903f9fa7bdf
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Linked notes

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