Hydrochloric Acid → 7-(2-Fluorobenzoyl)-indolin-2-one

HRID 2164299Notes

Reaction equation

HRID 2164299 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]2SC)=[O:5].[Sn].Cl>C(O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11]2)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 133942837-(2-Fluorobenzoyl)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 133942867-(2-Fluorobenzoyl)-indolin-2-oneYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 60 g (0.2 mole) of 7-(2-fluorobenzoyl)-3-methylthioindolin-2-one and 60 g (0.5 mole) of tin powder in one liter of 95% ethanol was heated to reflux and 150 ml of concentrated hydrochloric acid was added. Heating was continued for 18 hrs, then the mixture was cooled and the precipitate was collected by decanting the slurry from the remaining tin and filtering the slurry. The filter cake was recrystallized twice from absolute ethanol to give 31 g (60%) white needles, m.p. 209°-210° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureHeating
  4. temperaturethe mixture was cooled
  5. customthe precipitate was collected
  6. customby decanting the slurry from the remaining tin
  7. filtrationfiltering the slurry
  8. customThe filter cake was recrystallized twice from absolute ethanol

Sources & evidence

ORD record
ord-9c96ec57725541ba8227d135cad2204b
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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