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

HRID 427730Notes

Reaction equation

HRID 427730 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 (D9, 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-b923f37f5b92407e934ab00e29177827
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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