Methanol → 4-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamide

HRID 19587Notes

Reaction equation

HRID 19587 reaction equation
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH2:11])=[O:10])[C:5]=1[N+:12]([O-])=O)([CH3:3])[CH3:2].CO>[Ni].O>[NH2:12][C:5]1[C:6]([C:9]([NH2:11])=[O:10])=[N:7][NH:8][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 160997461H-Pyrazole-3-carboxamide, 5-(1-methylethyl)-4-nitro-

Product 1

HCID 160997494-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamideYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

To a solution of 5-isopropyl-4-nitropyrazol-3-carboxamide (2.57 g; 12.97 mmol), methanol (20 mL) and water (5 mL) was added 0.7 g Raney Ni (W5). The mixture was stirred under hydrogen atmosphere (760 torr) for four hours. The reaction mixture was filtered, the filtrate was concentrated to dryness in vacuo and the residue was recrystallized from ethyl acetate to yield 1.94 g (89%) of the product. The product was purified by chromatography on silica gel, the mixture of chloroform/methanol (97/3) was used as mobile phase. Yield 95%; mp=178-179° C.; MS (ES+): 169.1 (100%, M+H+). 1H NMR (CD3OD; 400 MHz): 1.31 d (6H; J=7.5 Hz), 3.06 sept (1H; J=7.5 Hz), 4.83 s (2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ced9d1d51268491a831fde3de0687dce
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Reaction notes

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