Methylhydrazine → methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate

HRID 406578Notes

Reaction equation

HRID 406578 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[C:10](=[C:15]([NH:17]C)[CH3:16])[C:11]([O:13][CH3:14])=[O:12].[CH3:20][NH:21]N>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:21]([CH3:20])[N:17]=[C:15]([CH3:16])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 178483602HCID 178483602, compound2×

Product 1

HCID 66614282methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 2-chloro-4-fluoro-α-[1-(methylamino)ethylidene]-β-oxobenzenepropanoate (i.e. the product of Step B) (15.91 g, 55.82 mmol) and methylhydrazine (3 mL, 56 mmol) in diethyl ether (150 mL) was stirred at room temperature for 48 h. The reaction mixture was concentrated under reduced pressure to provide the title compound as a colorless oil (15 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3095b6652304e58bf35eec1cd198032
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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