HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → 2-(4-Trifluoromethyl-phenyl)-nicotinoyl chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Lithium | HCID 3028194 | — |
| Reactant | 2-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester | HCID 53950991 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(4-Trifluoromethyl-phenyl)-nicotinoyl chloride | HCID 21253363 | — |
Reaction Steps
To a solution of the title B compound, 2-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (0.626 g, 2.228 mmol) in 1:1 THF:H2O (10 mL) is added LiOH.H2O (0.187 g, 4.456 mmol). After 3.5 h, the reaction mixture is concentrated to dryness under reduced pressure. To a slurry of the crude lithium salt in methylene chloride (10 mL) is added oxalyl chloride (0.78 mL, 8.91 mmol) followed by a few drops DMF. After stirring 16 h, the reaction mixture is concentrated to dryness under reduced pressure and used as is without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06197798B1 |
| Source dataset | uspto-grants-2001_03 |
| ORD ID | ord-a9c82025090045d295f54f6006b424bb |
| Source note | uspto-grants-2001_03 |