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

HRID 1421621Notes

Reaction equation

S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:15](C(OCC)=O)=[N:14]2)=[CH:9][CH:8]=1>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:15]=[N:14]2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Two mililiters (2 ml) of a mixture of sulfuric acid and water (v/v=1/1), and 0.5 g of 2-(4-chlorophenyl)-6-ethoxycarbonyl-5-trifluoromethylpyridazin-3-one (the present compound 1-51) were mixed and heated for 5 hours on a 150° C. oil bath. The reaction solution was cooled to room temperature, poured into water and extracted with 100 ml of ethyl acetate. The organic layer was washed with 50 ml of saturated sodium chloride solution twice and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained crystals were washed with 50 ml of n-hexane to afford 0.18 g of 2-(4-chlorophenyl)-5-trifluoromethylpyridazin-3-one (yield:45%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionextracted with 100 ml of ethyl acetate
washThe organic layer was washed with 50 ml of saturated sodium chloride solution twice
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
washthe obtained crystals were washed with 50 ml of n-hexane

Sources & evidence

ORD record: ord-e754356bbc0344028efcbef956b64108
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06077953

Reaction notes

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