methyl 1-methyl-3-nitro-1H-pyrazole-5-carboxylate → methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate

HRID 1918836Notes

Reaction equation

HRID 1918836 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]([N+:11]([O-])=O)=[N:3]1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:11][C:4]1[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 2

HCID 18916504methyl 1-methyl-3-nitro-1H-pyrazole-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13248993methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 250 mL Parr hydrogenation flask was placed methyl 1-methyl-3-nitro-1H-pyrazole-5-carboxylate, (530 mg, 2.9 mmol) dissolved in ethyl acetate (15 mL) and ethanol (15 mL), to which was added 10% Pd/C (Degussa type) (100 mg). The mixture was placed on the Parr apparatus and pressurized with hydrogen to 50 PSI and shaken for 2.5 hrs. The reaction was filtered through a pad of celite which was washed with ethyl acetate. The solvent was removed under vacuum to give 119a as a white solid (450 mg, 2.9 mmol, quantitative yield).

Workup

  1. filtrationThe reaction was filtered through a pad of celite which
  2. washwas washed with ethyl acetate
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2e6840a07b754b02bda836f48042426f
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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