Acetic Anhydride → HCID 86614793, compound

HRID 1361453Notes

Reaction equation

HRID 1361453 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]([OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[C:8]=2[C:14]([F:17])([F:16])[F:15])[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][CH:6]=[C:7]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=3)[C:8]=2[C:14]([F:17])([F:16])[F:15])[N:3]=[C:2]([CH3:1])[C:11]=1[CH3:12])(=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178432214HCID 178432214, compound

Product 1

HCID 86614793HCID 86614793, compound

Conditions

Temperature
122.5 °C

Procedure

A solution of 3.4 g of 4-(4-trifluoromethoxyphenoxy)-3-trifluoromethyl-aniline, 2.4 g of ethyl 2-methylacetoacetate, and 0.3 g of p-toluenesulfonic acid dissolved in 100 mL of xylene was heated under reflux for 36 hr. This reaction solution was cooled, and the precipitated crystals were collected by filtration to give 1.73 g of 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-7-trifluoromethyl-quinoline. The filtrate was concentrated under the reduced pressure to give 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline. Acetic anhydride (40 mL) was added to 2,3-dimethyl-4-hydroxy-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline obtained from the filtrate, 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 0.35 g of 4-acetoxy-2,3-dimethyl-6-(4-trifluoromethoxyphenoxy)-5-trifluoromethyl-quinoline.

Workup

  1. customobtained from the filtrate
  2. concentrationThis reaction solution was concentrated under the reduced pressure, ethyl acetate
  3. additionwas then added to the concentrate
  4. washthe mixture was washed with brine
  5. customThereafter, the solvent was removed under the reduced pressure
  6. 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-01b7bd8abd074ed5b72c072fb978c60a
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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