Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 136338343 | HCID 136338343 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 136338336 | HCID 136338336 | — |
Reaction Steps
To a suspension of 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (9.0 g, 24.64 mmol) in dichloromethane (120 mL) at 0° C. was added 5 drops of DMF. Oxalyl chloride (3.24 mL, 37.0 mmol) was added slowly. The mixture was stirred at 0° C. for 1 h. The mixture was warmed to room temperature, and an additional portion of oxalyl chloride (3.24 mL, 37.0 mmol) was added. The reaction mixture was stirred overnight. Methanol (50 mL) was added and the mixture was stirred overnight. The solvent was removed under reduced pressure to afford methyl 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification in the next step. MS (m/z) 380.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08658636B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-d80c10603faf493aa67228ffad493ab2 |
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| Source note | uspto-grants-2014_02 |
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