tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate → tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamate

HRID 336838Notes

Reaction equation

HRID 336838 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:5]=1

Participants

4

Reactant 1

HCID 135971896tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate

Product 1

HCID 45091900tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamateYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 5.88 g (25.77 mmol) of tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate diluted in 145 ml of methanol, are added under inert atmosphere 600 mg of palladium on charcoal (10%), then the reaction mixture is stirred under hydrogen atmosphere for 24 h. The solution is filtered on Celite and rinsed with ethyl acetate. The filtrate is concentrated to yield 4.93 g of tert-butyl 5-amino-1H-pyrazol-3-ylcarbamate in the form of a grey solid.

Workup

  1. filtrationThe solution is filtered on Celite
  2. washrinsed with ethyl acetate
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-de3ccc7e099243c3bccdcead3a155060
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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