Acetic Acid → Dimethyl-(6-trifluoromethyl-1H-indol-5-yl)amine

HRID 1258205Notes

Reaction equation

HRID 1258205 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[C:4]([C:15]([F:18])([F:17])[F:16])=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH2:9][C:10]#N)[CH:8]=1.C(O)C.C(O)(=O)C>[C].[Pd].O>[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16])[NH:12][CH:10]=[CH:9]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 58437521(5-Dimethylamino-2-nitro-4-trifluoromethylphenyl)acetonitrile

Product 1

HCID 58437283Dimethyl-(6-trifluoromethyl-1H-indol-5-yl)amineYield 119.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of (5-dimethylamino-2-nitro-4-trifluoromethylphenyl)acetonitrile (0.058 g) in a mixed solvent of ethanol (1 mL), acetic acid (0.1 mL) and water (0.1 mL) was added palladium-carbon powder (0.0058 g), and this mixture was stirred at 35° C. for 16 hours. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound (0.058 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-226364abaa3d46a59ba675898bf532c5
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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