1-(Tert-butyl)-4-nitro-1H-pyrazole → 1-(tert-butyl)-1H-pyrazol-4-amine

HRID 1930347Notes

Reaction equation

HRID 1930347 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([N:5]1[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 113557081-(Tert-butyl)-4-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 134698171-(tert-butyl)-1H-pyrazol-4-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-tert-butyl-4-nitro-1H-pyrazole (20 g, 118 mmol) and Pd/C (10%, 2 g, 1.9 mmol) in MeOH (100 mL) was hydrogenated under 1 atmosphere of hydrogen at RT for 16 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 1-tert-butyl-1H-pyrazol-4-ylamine (15 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ 7.08 (s, 1 H), 6.90 (s, 1H), 3.70 (s, 2 H), 1.41 (s, 9 H); MS (ESI) m/z: 140.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-802236db93ff44aba6bc6eab5070671c
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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