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

HRID 2276008

Reaction equation

HRID 2276008 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-f68676f0122141afb3a00f2295293e75
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Linked notes

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