m-Chlorophenylhydrazine hydrochloride → 1-(3-Chlorophenyl)-5-(5-trifluoromethoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930043Notes

Reaction equation

HRID 930043 reaction equation
[Li].[F:2][C:3]([F:22])([F:21])[O:4][C:5]1[CH:6]=[C:7]([C:11]([O-])=[CH:12][C:13](=O)[C:14]([O:16]CC)=[O:15])[CH:8]=[N:9][CH:10]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:46][C:47]1[CH:48]=[C:49]([NH:53][NH2:54])[CH:50]=[CH:51][CH:52]=1>>[Cl:46][C:47]1[CH:48]=[C:49]([N:53]2[C:11]([C:7]3[CH:8]=[N:9][CH:10]=[C:5]([O:4][C:3]([F:2])([F:21])[F:22])[CH:6]=3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[N:54]2)[CH:50]=[CH:51][CH:52]=1

Participants

4

Reactant 3

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735143Lithium 1-(5-trifluoromethoxypyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024411-(3-Chlorophenyl)-5-(5-trifluoromethoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

1.13 g (3.25 mmol) of the compound of Example 18A is reacted analogously to the synthesis of the compound of Example 20A with 874 mg (4.88 mmol) of 3-chlorophenylhydrazine hydrochloride. After hydrolysis, 609 mg (49% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-9851d5f71a22428486c5743ea029f7e9
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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