1-Methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide → 1-methyl-3-(4-aminophenyl)-1H-indole-2-carboxamide

HRID 230550Notes

Reaction equation

HRID 230550 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[C:3]1[C:20]([NH2:22])=[O:21]>[Pd].CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[C:3]1[C:20]([NH2:22])=[O:21]

Participants

4

Reactant 1

HCID 688244991-Methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide

Product 1

HCID 688263421-methyl-3-(4-aminophenyl)-1H-indole-2-carboxamideYield 506.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.2 g of 1-methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide and 0.14 g of 10% palladium-on-charcoal are added to 8 ml of methanol and the reaction mixture is hydrogenated under 5 bar for 4 hours and 30 minutes at 25° C. The reaction mixture is then filtered over a thin layer of silica gel and the filtrate is concentrated under reduced pressure, to give 0.91 g of 1-methyl-3-(4-aminophenyl)-1H-indole-2-carboxamide, the characteristics of which are as follows:

Workup

  1. filtrationThe reaction mixture is then filtered over a thin layer of silica gel
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f0b28bccee149b69a3820f74c89aa3e
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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