Hydrochloric Acid → 6-Fluoro-1,3-dihydro-5-methyl-2H-indol-2-one

HRID 2414100Notes

Reaction equation

HRID 2414100 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([F:13])[CH:7]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[F:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:2][C:3](=[O:4])[NH:5]2)=[CH:10][C:9]=1[CH3:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 23451182-chloro-N-(3-fluoro-4-methylphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135656696-Fluoro-1,3-dihydro-5-methyl-2H-indol-2-oneYield 2.9%

Procedure

An intimate mixture of 11.62 g (57.6 mmol) of N-(2-chloroacetyl)-3-fluoro-4-methylaniline and 30.6 g (229.5 mmol) of anhydrous aluminum chloride was heated to 210°-220° C. After 4 hours, the reaction mixture was cooled and then added to 100 ml of 1N hydrochloric acid and 50 ml of ice. A tan solid formed, which was collected by filtration and recrystallized from aqueous ethanol. Three crops were obtained, weighing 4.49 g, 2.28 g and 1.0 g, respectively. The crop weighing 1.0 g was further recrystallized from water to give 280 mg of the title compound, mp 168.5°-171° C.

Workup

  1. temperaturewas heated to 210°-220° C
  2. temperaturethe reaction mixture was cooled
  3. customA tan solid formed
  4. filtrationwhich was collected by filtration
  5. customrecrystallized from aqueous ethanol
  6. customThree crops were obtained
  7. customwas further recrystallized from water

Sources & evidence

ORD record
ord-0c0d327c313f4d83b98a40e444c6bc50
Source dataset
uspto-grants-1988_01
Patent number
US04721712

Reaction notes

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