Acetic Anhydride → 4-Acetoxy-2,3-dimethyl-6-(4-trifluoromethoxyphenoxy)-7-trifluoromethyl-quinoline
Reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]([OH:13])[C:9]2[C:4](=[CH:5][C:6]([C:26]([F:29])([F:28])[F:27])=[C:7]([O:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([O:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([C:26]([F:28])([F:29])[F:27])=[C:7]([O:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=[C:2]([CH3:1])[C:11]=1[CH3:12])(=[O:32])[CH3:31]Participants
3
Conditions
- Temperature
- 122.5 °C
Procedure
Acetic anhydride (40 mL) was added to 1.73 g of 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-7-trifluoromethyl-quinoline obtained as crystals, and the mixture was heated at 120 to 125° C. for one hr. This reaction solution was concentrated under the reduced pressure, ethyl acetate was then added to the concentrate, and the mixture was washed with brine. Thereafter, the solvent was removed under the reduced pressure, and the crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 0.82 g of 4-acetoxy-2,3-dimethyl-6-(4-trifluoromethoxyphenoxy)-7-trifluoromethyl-quinoline.
Workup
- customobtained as crystals
- concentrationThis reaction solution was concentrated under the reduced pressure, ethyl acetate
- additionwas then added to the concentrate
- washthe mixture was washed with brine
- customThereafter, the solvent was removed under the reduced pressure
- customthe crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-d7bcd846516147a7ac62bcf04da4e391
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880006B2
Reaction notes
Loading…