Hydrochloric Acid → 2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-cyano-5-trifluoromethylpyridazin-3-one

HRID 2289845Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][N:13]=[CH:14][C:15](=O)[C:16]([F:19])([F:18])[F:17])=[C:4]([F:21])[CH:3]=1.[C:22]([CH2:24][C:25](OCC)=[O:26])#[N:23].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:25](=[O:26])[C:24]([C:22]#[N:23])=[C:15]([C:16]([F:19])([F:18])[F:17])[CH:14]=[N:13]2)=[C:4]([F:21])[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

After 4.345 g of 3, 3, 3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone) was dissolved in 20 mL of pyridine, 2.1 mL of ethyl cyanoacetate was added to the pyridine solution, which was followed by stirring for 4 hours at 120° C. After cooling to room temperature, the reaction solution was poured into 3N-hydrochloric acid and extracted with diethyl ether. After the organic layer was washed with aqueous saturated sodium bicarbonate and concentrated, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane=2/8) to afford 2.858 g of 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-5).

Workup

temperatureAfter cooling to room temperature
extractionextracted with diethyl ether
washAfter the organic layer was washed with aqueous saturated sodium bicarbonate
concentrationconcentrated

Sources & evidence

ORD record: ord-797ea77963fb4a1ab19582d561808973
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093818

Reaction notes

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