tert-Butyl 7-nitro-1H-indazole-1-carboxylate → tert-Butyl 7-amino-1H-indazole-1-carboxylate

HRID 482344

Reaction equation

HRID 482344 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:10]=[CH:9]2)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:10]=[CH:9]2

Participants

4

Reactant 1

HCID 15606021tert-Butyl 7-nitro-1H-indazole-1-carboxylate

Product 1

HCID 19063674tert-Butyl 7-amino-1H-indazole-1-carboxylateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-Nitro-1-tert-butoxycarbonyl-indazole (1.000 g, 3.798 mmol), prepared as in Intermediate 25, and palladium on carbon (10 wt %, 0.10 g) in ethyl acetate (25 mL) at ambient temperature is stirred under atmospheric hydrogen overnight. The mixture is filtered through celite and concentrated in vacuo to an oil which solidified under high vacuum to provide the title compound as a purple solid (0.860 g, 3.686 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.59 (b, 9H); 6.13 (b, 2H); 6.76 (d, J=7.6 Hz, 1H); 6.97 (d, J=7.6 Hz, 1H); 7.04-7.07 (m, 1H); 8.24 (s, 1H). TLC: Rf =0.47 (25:75 ethyl acetate: n-hexane).

Workup

  1. filtrationThe mixture is filtered through celite and
  2. concentrationconcentrated in vacuo to an oil which

Sources & evidence

ORD record
ord-1c98404b27ed402791ff60fcc610f772
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Linked notes

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