5-Nitroindazole → 1H-Indazol-5-amine

HRID 2042105Notes

Reaction equation

HRID 2042105 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-])=O>CO.[Pd]>[NH:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

4

Reactant 1

HCID 215015-Nitroindazole

Product 1

HCID 880121H-Indazol-5-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-1H-indazole (50 g, 0.31 mol) and 10% Pd/C (5.0 g) in MeOH (400 mL) was heated under H2 (30 psi) atmosphere overnight. After the mixture was filtered, the filtrate was concentrated to give 1H-indazol-5-ylamine as a yellow solid (40 g, 97% yield). 1H NMR (300 MHz, DMSO-d6) δ 12.50 (br s, 1H), 7.70 (s, 1H), 7.22 (d, J=6.6 Hz, 1H), 6.77 (d, J=6.6 Hz, 1H), 6.74 (s, 1H), 4.72 (br s, 1H); MS (ESI) m/z: 134.2 (M+H+).

Workup

  1. temperaturewas heated under H2 (30 psi) atmosphere overnight
  2. filtrationAfter the mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5e3d3b282aa6458a916eee4f88e42d0c
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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