Pyridine → 3,5-dimethyl-1-m-tolyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 8069

Reaction equation

HRID 8069 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[CH2:11]([O:13][C:14](=[O:22])[CH:15]([C:19](=O)[CH3:20])[C:16](=O)[CH3:17])[CH3:12].N1C=CC=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[C:16]([CH3:17])=[N:9][N:8]([C:4]2[CH:3]=[C:2]([CH3:10])[CH:7]=[CH:6][CH:5]=2)[C:19]=1[CH3:20])=[O:22])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 71562m-Tolylhydrazinium(1+) chlorideHCID 79063Ethyl 2-acetylacetoacetate

Product 1

HCID 98783353,5-dimethyl-1-m-tolyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similar to Example 1, equimolar amounts of m-tolylhydrazine hydrochloride and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of a 50% pyridine in ethanol. The resulting oil was purified by flash chromatography to yield the named product as a solid (m.p. 46.5° C.–47.5° C.).

Workup

  1. customThe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-10ff9f3ebf424ef1bf07a369dc0fa429
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Linked notes

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