ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate → ethyl 7-amino-5-(trifluoromethoxy)-1H-indole-2-carboxylate

HRID 2238971Notes

Reaction equation

HRID 2238971 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:18][C:19]([F:22])([F:21])[F:20])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2)([O-])=O>[C].[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]([O:18][C:19]([F:22])([F:20])[F:21])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2

Participants

4

Reactant 1

HCID 57476182ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate

Product 1

HCID 57476183ethyl 7-amino-5-(trifluoromethoxy)-1H-indole-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate (3.06 g), 10% palladium-carbon (50% containing water, 600 mg) and tetrahydrofuran (150 mL) was subjected to catalytic reduction under hydrogen atmosphere at normal pressure. The palladium-carbon was removed by filtration, and the filtrate was concentrated. The obtained crystals were washed with hexane to give the title compound (2.63 g, yield 95%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point 190-191° C.

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-7b39cb97f0d04289bfa398db37367c16
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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