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

HRID 1589395Notes

Reaction equation

HRID 1589395 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, m.p. 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-4d1c30502bce4609ad368f5408f7747c
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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