Tert-butyl 5-nitro-1H-indole-1-carboxylate → tert-Butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate

HRID 1517943Notes

Reaction equation

HRID 1517943 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=[CH:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 11680504Tert-butyl 5-nitro-1H-indole-1-carboxylate

Product 1

HCID 22240520tert-Butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.8 g tert-butyl 5-nitro-indole-1-carboxylate are dissolved in 120 ml of methanol. 600 mg palladium on charcoal (10%) are added thereto and the mixture is hydrogenated for 1.5 hours at ambient temperature. Then the catalyst is filtered off and the solvent is eliminated in vacuo.

Workup

  1. filtrationThen the catalyst is filtered off

Sources & evidence

ORD record
ord-90c49f8e0d0f42c9807d3881fcf860b2
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

Loading…