1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxamide → 4-amino-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 72185

Reaction equation

HRID 72185 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:10]([O-])=O)[C:4]([CH3:13])=[N:3]1>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:10][C:5]1[C:4]([CH3:13])=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 1

HCID 12297641,3-dimethyl-4-nitro-1H-pyrazole-5-carboxamide

Product 1

HCID 138229254-amino-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 97.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxamide (730 mg, 3.96 mmol) in anhydrous ethanol (100 mL) and ethyl acetate (100 mL) was added 10 wt % Pd on carbon (100.0 mg). The reaction mixture was evacuated with vacuum and purged with H2 (3×), then stirred under H2 at 50 psi for 5 hours. The reaction mixture was then filtered through a pad of Celite®. The filtrate was concentrated in vacuo and the crude was purified by column chromotagraphy (Si-PPC, gradient 0 to 30% methanol in dichloromethane) to get the desired product (597.0 mg, 97.7%) as a solid. 1H NMR (DMSO-d6, 400 MHz) δ ppm 7.26 (br s, 2H), 4.03 (br s, 2H), 3.84 (s, 3H), 2.02 (s, 3H); LC-MS m/z (method A)=155.2 [M+H]+, RT=0.35 min.

Workup

  1. customThe reaction mixture was evacuated with vacuum
  2. custompurged with H2 (3×)
  3. filtrationThe reaction mixture was then filtered through a pad of Celite®
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude was purified by column chromotagraphy (Si-PPC, gradient 0 to 30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-81c88674567548589f2b42bc6eb3856d
Source dataset
uspto-grants-2014_09
Patent number
US08828990B2

Linked notes

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