1-Methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamide → 4-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

HRID 1108474Notes

Reaction equation

HRID 1108474 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:10]([O-])=O)[C:4]([CH2:13][CH2:14][CH3:15])=[N:3]1.[H][H]>[Pd].C(OCC)(=O)C>[NH2:10][C:5]1[C:4]([CH2:13][CH2:14][CH3:15])=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 27544921-Methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 33380444-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 1-methyl-4-nitro-3-n-propylpyrazole-5-carboxamide (EP-A-0463756; 237.7 g, 1.12 mol) and 5% palladium on charcoal (47.5 g) in ethyl acetate (2.02 l) was hydrogenated at 344.7 kPa (50 psi) and 50° C. for 4 hours, when the uptake of hydrogen was complete. The cool reaction mixture was filtered, then the filter pad washed with ethyl acetate, the combined filtrate and washings thus furnishing an ethyl acetate solution of the title compound (EP-A-0463756) which was of sufficient purity to use directly in the next stage of the reaction sequence (see Preparation 4).

Workup

  1. customThe cool reaction mixture
  2. filtrationwas filtered
  3. washthe filter pad washed with ethyl acetate

Sources & evidence

ORD record
ord-3f30ade9fc4640979157a74da85fe7b7
Source dataset
uspto-grants-2000_05
Patent number
US06066735

Reaction notes

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