Acetic Acid → 2-(4-Chlorophenyl)-4-methyl-5-trifluoromethylpyridazin-3-one

HRID 2271238Notes

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.[CH3:17][CH:18](C(O)=O)[C:19](O)=[O:20].N1CCCCC1.C(O)(=O)C>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:19](=[O:20])[C:18]([CH3:17])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

First, 0.25 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chlorophenylhydrazone), compound 3-11 was dissolved in 2 ml of pyridine. To this solution were added 0.24 g of methylmalonic acid and 0.09 g of piperidine, and the mixture was stirred at 80° C. for 4 hours. Then, 2.0 ml of acetic acid was added, and the mixture was stirred at 80° C. for 6.5 hours and further at 120° C. for 4 hours. After completion of the reaction, the reaction solution was poured into water, and this mixture was extracted with diethyl ether. The organic layer was washed with water and then with diluted hydrochloric acid, dried with anhydrous magnesium sulfate, and evaporated to remove the diethyl ether. The residue was subjected to silica gel column chromatography to give 0.15 g of 2-(4-chlorophenyl)-4-methyl-5-trifluoromethylpyridazin-3-one, compound 5-12, m.p., 80.8° C.

Workup

stirringthe mixture was stirred at 80° C. for 6.5 hours and further at 120° C. for 4 hours
customAfter completion of the reaction
extractionthis mixture was extracted with diethyl ether
washThe organic layer was washed with water
dry with materialwith diluted hydrochloric acid, dried with anhydrous magnesium sulfate
customevaporated
customto remove the diethyl ether

Sources & evidence

ORD record: ord-ca8e743d3f7b478e9beac72bd9c140aa
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333413B1

Reaction notes

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