m-Chlorophenylhydrazine hydrochloride → 1-(3-chlorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1011946

Reaction equation

HRID 1011946 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][CH2:12][O:13][C:14]([CH:16]([C:20]([CH3:22])=O)[C:17]([CH3:19])=O)=[O:15]>>[CH2:12]([O:13][C:14]([C:16]1[C:17]([CH3:19])=[N:10][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[C:20]=1[CH3:22])=[O:15])[CH3:11]

Participants

3

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 79063Ethyl 2-acetylacetoacetate

Product 1

HCID 99654721-(3-chlorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 58%

Procedure

In analogy to the procedure described in Example 38A], 3-chlorophenylhydrazine hydrochloride and ethyl diacetoacetate gave the title compound after purification by flash column chromatography (n-heptane:EtOAc 9:1-1:1) in 58% yield as light yellow solid. MS: 279.0 (MH+, 1 Cl).

Sources & evidence

ORD record
ord-59f743d999b741b3a2f97438755cde7a
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Linked notes

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