tert-butyl 4-nitro-1H-pyrazole-1-carboxylate → tert-butyl 4-amino-1H-pyrazole-1-carboxylate

HRID 714998Notes

Reaction equation

HRID 714998 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1

Participants

5

Reactant 2

HCID 66765764tert-butyl 4-nitro-1H-pyrazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59587648tert-butyl 4-amino-1H-pyrazole-1-carboxylateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-nitro-1H-pyrazole-1-carboxylate (1.0 g, 4.7 mmol) in MeOH (120 ml) was passed through the H-Cube with full hydrogen mode at 60° C. and 1 bar with a 10% Pd/C cartridge using 1 ml/min flow rate. The solution was then passed through the H-Cube for a second time using identical conditions and the solvent removed in vacuo to afford tert-butyl 4-amino-1H-pyrazole-1-carboxylate (0.82 g, 4.5 mmol, 95%). 1H NMR (DMSO) δ 1.54 (9H, s), 4.42 (2H, s), 7.33 (1H, s), 7.35 (1H, s). LCMS (2) Rt: 1.45 min; m/z (ES+) 206 M+Na+.

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0dca8df094df40cead42b1814cf91325
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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