Methanol → Methyl 1-(4-aminophenyl)-1H-pyrazole-4-carboxylate

HRID 1977289Notes

Reaction equation

HRID 1977289 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].[NH4+].[Cl-].CO>[Fe].O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 11637370HCID 11637370, compound

Product 1

HCID 57210789Methyl 1-(4-aminophenyl)-1H-pyrazole-4-carboxylateYield 57.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-nitrophenyl)-1H-pyrazol-4-carboxylic acid methyl ester (19.44 g), Fe powder, NH4Cl, methanol and H2O was heated for 30 minutes at 80° C. for 3 hours at 100° C. The reaction mixture was concentrated by evaporation, added into dichloromethane, and was filtered. The filtrate was extracted with water, dried over magnesium sulfate and concentrated by evaporation to give 1-(4-aminophenyl)-1H-pyrazol-4-carboxylic acid methyl ester (9.84 g).

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. additionadded into dichloromethane
  3. filtrationwas filtered
  4. extractionThe filtrate was extracted with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-04e3e676a7a24bac88703dc78c45d21a
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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