Methanol → 6-(Trifluoromethyl)indolin-5-ol

HRID 840544Notes

Reaction equation

HRID 840544 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][CH2:7][CH2:6]2.I[Si](C)(C)C.CO>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:13])[F:14])[NH:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 112067135-Methoxy-6-(trifluoromethyl)indoline

Product 1

HCID 226198656-(Trifluoromethyl)indolin-5-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-methoxy-6-trifluoromethylindoline (D3, 7.5 g, 34.3 mmol) and iodotrimethylsilane (12.5 ml, 89.3 mmol) in dry chloroform (70 ml) was heated under reflux for 65 h. Methanol was then added cautiously with stirring to the cooled mixture, and solvent was then removed in vacuo. The residue was treated with saturated sodium bicarbonate solution and water until basic, and then extracted with dichloromethane/methanol. The organic extract was washed with brine, dried and evaporated. The residue was extracted with ether in a Soxhlet apparatus, and concentration of the resultant solution gave the title compound in three crops (total 2.85 g, 41%), m.p.>180° (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 65 h
  3. customwas then removed in vacuo
  4. additionThe residue was treated with saturated sodium bicarbonate solution and water until basic, and
  5. extractionthen extracted with dichloromethane/methanol
  6. extractionThe organic extract
  7. washwas washed with brine
  8. customdried
  9. customevaporated
  10. extractionThe residue was extracted with ether in a Soxhlet apparatus, and concentration of the resultant solution

Sources & evidence

ORD record
ord-16cd1aa91eb54a9c8567231637aba63e
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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