5-Nitroindole → 5-Aminoindole

HRID 70069

Reaction equation

HRID 70069 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-])=O.C1(C2CCN(C(C3C=C(OC)C(OC)=C(OC)C=3)=O)CC2)C=CC=CC=1>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 225235-NitroindoleHCID 39582222(4-Phenylpiperidin-1-yl)(3,4,5-trimethoxyphenyl)methanone

Product 1

HCID 788675-AminoindoleYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-nitro-1H-indole (11 g, 67.9 mmol) and Pd/C (5%; 1g), dissolved in ethanol (50 mL), was hydrogenated for 3 h at 40 psi. The reaction mixture was filtered and the excess of ethanol was evaporated under reduced pressure. Solid product was recrystallized from hexane to obtain the pure compound 5-aminoindole (55-1). Yield: 92.5%. 1H NMR (500 MHz, CDCl3): δ 7.96 (br, 1H), 7.20 (d, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 6.67 (dd, 1H), 6.37 (s, 1H), 3.50 (s, 2H). MS (ESI) m/z 133.0 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe excess of ethanol was evaporated under reduced pressure
  3. customSolid product was recrystallized from hexane

Sources & evidence

ORD record
ord-ed2f14d75d3b46958858df77ec7402b5
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Linked notes

Loading…