tert-Butyl 2-(3-nitro-1H-pyrazol-1-yl)acetate → tert-butyl 2-(3-amino-1H-pyrazol-1-yl)acetate

HRID 545989Notes

Reaction equation

HRID 545989 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[N:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:16])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66712097tert-Butyl 2-(3-nitro-1H-pyrazol-1-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 62111572tert-butyl 2-(3-amino-1H-pyrazol-1-yl)acetateYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Conditions

Temperature
25 °C

Procedure

To a solution containing (3-nitro-pyrazol-1-yl)-acetic acid tert-butyl ester (104 mg, 0.46 mmol) in methanol (3 mL), palladium, 10 wt. % on activated carbon, wet (˜50 mg) was added to the solution. The vial was charged with hydrogen gas (via balloon) and the mixture was stirred for 16 h at 25° C. The mixture was passed through a plug of celite and concentrated in vacuo to give the desired (3-amino-pyrazol-1-yl)-acetic acid tert-butyl ester (80 mg, 89%) as a light blue oil: ESI-LRMS m/e calcd for C9H15N3O2 [M+] 197.1, found 395.2 [2M+H+].

Workup

  1. additionwas added to the solution
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1903e2f71d2146e4b1f9d28adef04303
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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