Acetic Acid → 1H-Indol-5-ol, 6-(trifluoromethyl)-

HRID 1791674Notes

Reaction equation

HRID 1791674 reaction equation
C([O:8][C:9]1[C:10]([C:21]([F:24])([F:23])[F:22])=[CH:11][C:12]([N+:18]([O-])=O)=[C:13]([CH2:15][C:16]#N)[CH:14]=1)C1C=CC=CC=1.O.C(O)(=O)C>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][C:10]=1[C:21]([F:24])([F:23])[F:22])[NH:18][CH:16]=[CH:15]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22030888HCID 22030888, compound

Product 1

HCID 220307041H-Indol-5-ol, 6-(trifluoromethyl)-Yield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Benzyloxy-2-nitro-4(trifluoromethyl)phenylacetonitrile (2.22 g, 6.6 mmol) was dissolved in ethanol (45 ml), water (5 ml) and acetic acid (0.32 ml) then hydrogenated with 10% palladium on carbon at 1 atmosphere pressure for 2 hours. The catalyst was filtered off and filtrate evaporated to give 5-hydroxy-6-trifluoromethylindole (1.12 g, 84%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customfiltrate evaporated

Sources & evidence

ORD record
ord-6840e0bf182b4e299ed28de5d2ff9819
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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