5-Nitroindazole → 1H-Indazol-5-amine

HRID 1696508Notes

Reaction equation

HRID 1696508 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 (25 g, 0.153 mmol, commercially available) and 10% Pd/C (2.0 g) in MeOH was stirred under H2 (1 atm) overnight. After filtration, the filtrate was concentrated to yield 20 g (97%) of 1H-indazol-5-amine as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 12.50 (brs, 1H), 7.70 (s, 1H), 7.21 (d, J=8.7 Hz, 1H), 6.77 (d, J=8.7 Hz, 1H), 6.74 (s, 1H), 4.71 (brs, 1H), 3.15 (d, J=4.8 Hz, 2H); MS (ESI) m/z: 134 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-02a0b5f926f247038418fad70f4ae852
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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