m-Chlorophenylhydrazine hydrochloride → 1-(3-Chlorophenyl)-5-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930045Notes

Reaction equation

HRID 930045 reaction equation
[Li].[Cl:2][C:3]1[CH:8]=[C:7]([C:9]([O-])=[CH:10][C:11](=O)[C:12]([O:14]CC)=[O:13])[CH:6]=[CH:5][N:4]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:42][C:43]1[CH:44]=[C:45]([NH:49][NH2:50])[CH:46]=[CH:47][CH:48]=1>>[Cl:42][C:43]1[CH:44]=[C:45]([N:49]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([Cl:2])[CH:8]=3)=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[N:50]2)[CH:46]=[CH:47][CH:48]=1

Participants

4

Reactant 3

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735144Lithium 1-(2-chloropyridin-4-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024421-(3-Chlorophenyl)-5-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

560 mg (2.14 mmol) of the compound of Example 19A is reacted analogously to the synthesis of the compound of Example 20A with 422 mg (2.36 mmol) of 3-chlorophenylhydrazine hydrochloride. After hydrolysis, 494 mg (69% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-bf5abfd5c98b43b89ed41cd52e4302a4
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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