tert-Butyl 4-nitro-1H-indazole-1-carboxylate → tert-Butyl 4-amino-1H-indazole-1-carboxylate

HRID 2101676Notes

Reaction equation

HRID 2101676 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 59233580tert-Butyl 4-nitro-1H-indazole-1-carboxylate

Product 1

HCID 34176514tert-Butyl 4-amino-1H-indazole-1-carboxylateYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 4-nitro-1H-indazole-1-carboxylate (1.2 g) was dissolved in ethanol (150 ml) and stirred with 10% palladium on carbon (0.24 g) under an atmosphere of hydrogen (1 atmosphere pressure) for 18 h. The solution was filtered through a pad of celite and the filtrate concentrated in vacuo to give the title compound as a yellow-orange solid (1.03 g).

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ac0c81a5fe944f0f82b75a9faca18b61
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

Loading…