Ethyl 4-hydrazinylbenzoate → ethyl 4-[5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoate

HRID 1696601

Reaction equation

HRID 1696601 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1)[CH3:2].[F:14][C:15]([F:22])([F:21])[C:16](=O)[CH2:17][C:18]#[N:19]>>[NH2:19][C:18]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:6][CH:7]=2)[N:12]=[C:16]([C:15]([F:22])([F:21])[F:14])[CH:17]=1

Participants

3

Reactant 2

HCID 792992Ethyl 4-hydrazinylbenzoateHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 58851394ethyl 4-[5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoateYield 91%

Procedure

Using the same method as Example QQ, 4-hydrazinobenzoic acid ethyl ester (From Example A82, 3.0 g, 16.6 mmol) and commercially available 1N NH 4,4,4-trifluoro-3-oxobutyronitrile (3.4 g, 24.9 mmol) were combined to afford ethyl 4-[5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoate (4.5 g, 91% yield), which was used to the next reaction without further purification.

Sources & evidence

ORD record
ord-d0506939fe5648ebaa6b86dd2efa9695
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Linked notes

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