Hydrazine → ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylate

HRID 1466552Notes

Reaction equation

HRID 1466552 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH:19]=1)[C:7]([C:9](=[CH:15][N:16](C)C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O.[NH2:22]N>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:7]2[NH:22][N:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66847508Ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylate

Product 1

HCID 66677632ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylate (2.49 g, 8.00 mmol, 1 eq) and hydrazine (0.40 mL, 13 mmol, 1.6 eq) in 20 mL ethanol was heated at 70° C. for 2 hours. Solvent and excess hydrazine were then evaporated to provide ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylate, which was used without further purification. LCMS (ESI) m+H=281.3.

Workup

  1. customSolvent and excess hydrazine were then evaporated

Sources & evidence

ORD record
ord-45ea6379dec34a02966fbbd6fd6f092c
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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