HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-cyano-5-trifluoromethylpyridazin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl cyanoacetate | HCID 7764 | — |
| Reactant | 3,3,3-Trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone) | HCID 69141430 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-cyano-5-trifluoromethylpyridazin-3-one | HCID 18699031 | — |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06093818 |
| Source dataset | uspto-grants-2000_07 |
| ORD ID | ord-797ea77963fb4a1ab19582d561808973 |
| Source note | uspto-grants-2000_07 |