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

HRID 1526110Notes

Reaction equation

HRID 1526110 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>[Pd].CO>[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

600 mg (10%) palladium on carbon is added under inert atmosphere to 5.88 g (25.77 mmol) of tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate diluted in 145 ml of methanol and then the reaction mixture is stirred under hydrogen atmosphere for 24 hours. The solution is filtered on Celite and then rinsed with ethyl acetate. The filtrate is concentrated to yield 4.93 g (96%) of tert-butyl 5-amino-1H-pyrazol-3-ylcarbamate in the form of a gray solid.

Workup

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

Sources & evidence

ORD record
ord-ab1d4f2a85984f52b356a052af06653e
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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