1H-Indole, 1-methyl-5-nitro- → 1-methyl-1H-indol-5-amine

HRID 1720876Notes

Reaction equation

HRID 1720876 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1>[Pd].C(O)C>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[CH:4]2

Participants

4

Reactant 1

HCID 1473221H-Indole, 1-methyl-5-nitro-

Product 1

HCID 27695641-methyl-1H-indol-5-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the nitroindole (D1) (5 g; 28.4 mmol) and 5% palladium on charcoal in ethanol (300 ml) was hydrogenated at 60 p.s.i. (4.14×105Pa) at room temperature for 3 h. Removal of the catalyst by filtration followed by evaporation of the solvent gave the title compound (3.39 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-ee2350dba4f848709c2bb503acd378bb
Source dataset
uspto-grants-1996_04
Patent number
US05508288

Reaction notes

Loading…