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

HRID 474330Notes

Reaction equation

HRID 474330 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](C)=[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.[NH2:21]N.[CH2:23]([OH:25])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:23])=[C:6]([C:7]2[NH:21][N:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 66677099Ethyl 2-(5-chloro-2-methylbenzoyl)-3-(dimethylamino)acrylate

Product 1

HCID 66677632ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylateYield 100%

Procedure

A solution of ethyl 2-(5-chloro-2-methylbenzoyl)-3-(dimethylamino)acrylate (2.87 g, 9.70 mmol) and hydrazine (0.50 mL, 16.0 mmol, 1.6 equiv) in 30 mL ethanol was heated at 70° C. for 2 hours. Solvent and excess hydrazine were then evaporated to provide 2.57 g (100%) of ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylate, which was used without further purification. LCMS (ESI) m+H=265.2.

Workup

  1. customSolvent and excess hydrazine were then evaporated

Sources & evidence

ORD record
ord-5ff200cee25c43c297391cb3c8ff29dc
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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