HCID 178499180, compound → HCID 178499176, compound

HRID 1012157Notes

Reaction equation

HRID 1012157 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[CH:8][NH:7][N:6]=1)=[O:4]>[Pd].C(O)C.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][NH:7][N:6]=1)=[O:4]

Participants

5

Reactant 1

HCID 178499180HCID 178499180, compound

Product 1

HCID 178499176HCID 178499176, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (10 g, 58 mmol) and 10% palladium on carbon (500 mg) in ethanol (150 ml) and DMF (30 ml) stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through celite reduced in vacuo and dried through azeotrope with toluene and methanol to afford 4-amino-1H-pyrazole-3-carboxylic acid methyl ester as a dark amber tar (9.35 g). (LC/MS (acidic): Rt 0.39 min, [M+H]+ 142).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. dry with materialdried through azeotrope with toluene and methanol

Sources & evidence

ORD record
ord-f5f1d8a3121f4ec78d128036713e4f2a
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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