1-methyl-5-(2-nitro-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester → ethyl 5-(2-aminophenylamino)-1-methyl-1H-pyrazole-4-carboxylate

HRID 220794

Reaction equation

HRID 220794 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:21])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:21])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 145905801-methyl-5-(2-nitro-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 57555331ethyl 5-(2-aminophenylamino)-1-methyl-1H-pyrazole-4-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Methyl-5-(2-nitro-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester (20.8 g, 72 mmol) from Example E11.1 was dissolved in methanol (330 ml) and hydrogenated over 10% Pd/C catalyst for 4 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo to give a white solid identified as the title compound (16.2 g, 87%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a white solid

Sources & evidence

ORD record
ord-cfec285de329481d9d44a6e2de2b0bb0
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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