Methylhydrazine → 3-Benzyl-1,5-dimethyl-1h-pyrazole-4-carboxylic acid methyl ester

HRID 2279641Notes

Reaction equation

HRID 2279641 reaction equation
[CH3:1][NH:2][NH2:3].[CH3:4][O:5][C:6](=[O:20])[CH:7]([C:17](=O)[CH3:18])[C:8](=O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCO>[CH3:4][O:5][C:6]([C:7]1[C:17]([CH3:18])=[N:3][N:2]([CH3:1])[C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:20].[CH3:4][O:5][C:6]([C:7]1[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3][N:2]([CH3:1])[C:17]=1[CH3:18])=[O:20]

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 595798522-Acetyl-3-oxo-4-phenyl-butyric acid methyl ester

Product 2

HCID 154462233-Benzyl-1,5-dimethyl-1h-pyrazole-4-carboxylic acid methyl esterHCID 154462275-benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

MeNHNH2 (0.42 mL. 7.9 mmol) is added to a solution of 2-acetyl-3-oxo-4-phenyl-butyric acid methyl ester (1.84 g, 7.85 mmol) in EtOH (15 mL) at RT. The mixture is stirred for 14 h at RT. The solvent is removed and crude material is purified by column chromatography using 10-25% EtOAc in hexane to afford 5-benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid methyl ester (less polar) and 3-benzyl-1,5-dimethyl-1H-pyrazole-4-carboxylic acid methyl ester (more polar).

Workup

  1. customThe solvent is removed
  2. customcrude material is purified by column chromatography

Sources & evidence

ORD record
ord-d3a3891bbe6e4d48896138129e88345c
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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