Triethyl phosphonoacetate → 2-(4-Chlorophenyl)-5-trifluoromethylpyridazin-3-one

HRID 1018443Notes

Reaction equation

HRID 1018443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[CH:4][CH:3]=1.[CH2:17]([O:19]P(CC(OCC)=O)(OCC)=O)[CH3:18]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:19])[CH:18]=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13345Triethyl phosphonoacetateHCID 691428133,3,3-Trifluoro-2-oxopropanal 1-(4-chlorophenylhydrazone)

Product 1

HCID 110548972-(4-Chlorophenyl)-5-trifluoromethylpyridazin-3-oneYield 52.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

First, 2 g of 3,3,3-trifluoro-2-oxo-1-propanal 1-(4-chlorophenylhydrazone) and 2 g of ethyl diethylphosphonoacetate were mixed with 20 ml of triethylamine, and the reaction was allowed to proceed at 50° C. for 24 hours. The solvent was distilled out under reduced pressure, and the residue was subjected to column chromatography, which afforded 1.16 g of 2-(4-chlorophenyl)-5-trifluoromethylpyridazin-3-one (compound 1-332).

Workup

  1. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-11f1982b801146359a6301d7beb892ce
Source dataset
uspto-grants-2002_11
Patent number
US06482773B1

Reaction notes

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