HCID 178470496, compound → HCID 178470494, compound

HRID 20308Notes

Reaction equation

HRID 20308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([NH2:11])=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 178470496HCID 178470496, compound

Product 1

HCID 178470494HCID 178470494, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150 ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-1H-pyrazole-3-carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz, DMSO-d6) δ 12.7 (s, 1H), 7.1 (s, 1H), 4.8 (s, 2H), 4.3 (q, 2H), 1.3 (t, 3H)).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record
ord-cb121feeaaa14482b15f3f54372c53e3
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Reaction notes

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