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

HRID 1906574Notes

Reaction equation

HRID 1906574 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 first two crops comprised a mixture of isomers (4-fluoro-5-methyl and 6-fluoro-5-methyl-2-oxindoles). 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-94e07966321b44c6a57b3c92690bf04d
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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