1-Methyl-4-nitro-1H-indole → 1-methyl-1H-indol-4-amine

HRID 1728595Notes

Reaction equation

HRID 1728595 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1>[Pd].C(O)C>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]2[CH3:1]

Participants

4

Reactant 1

HCID 131680671-Methyl-4-nitro-1H-indole

Product 1

HCID 221703071-methyl-1H-indol-4-amineYield 106%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the nitroindole (D9) (0.5 g; 2.8 mM) and 5% palladium on charcoal in ethanol (75 ml) was hydrogenated at 60 p.s.i. (4.14×105Pa) at room temperature for 2 h. Removal of the catalyst by filtration followed by evaporation of the solvent gave the title compound (0.44 g; 97%).

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration
  3. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-6215b06473fb40efbed4991a7a038cf8
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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