6-Nitroindazole → 1H-Indazol-6-amine

HRID 1696504Notes

Reaction equation

HRID 1696504 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=2)[CH:8]=[N:9]1

Participants

4

Reactant 1

HCID 242396-Nitroindazole

Product 1

HCID 814231H-Indazol-6-amineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-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 1H-indazol-6-ylamine (18.5 g, 94% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 12.20 (br s, 1H), 7.70 (s, 1H), 7.35 (d, J=5.4 Hz, 1H), 6.49-6.44 (m, 2H), 5.17 (brs, 2H). MS (ESI) m/z: 134 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3865f47a95b64a1fa0836ebfa94e1818
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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