Acetic Anhydride → HCID 67290904, compound

Temperature

100 °C

A mixture of 3-(2,2,2-trifluoroethoxy)-5,6,7,8-tetrahydroquinoline 1-oxide (530 mg, 2.1 mmol) and acetic anhydride (3 mL) was stirred at 100° C. for 2 hours. After cooling to room temperature, acetic anhydride was removed in vacuo. To the residue, methanol (5 mL) and potassium carbonate (1.77 g, 13 mmol) were added, and the mixture was stirred at room temperature for 20 hours. Then, methanol was evaporated in vacuo. To the residue was added ethyl acetate, and the mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1-1:2) to give 193 mg (36% yield) of the title compound as a white solid:

1. temperatureAfter cooling to room temperature
2. customacetic anhydride was removed in vacuo
3. stirringthe mixture was stirred at room temperature for 20 hours
4. customThen, methanol was evaporated in vacuo
5. additionTo the residue was added ethyl acetate
6. filtrationthe mixture was filtered through a pad of Celite
7. concentrationThe filtrate was concentrated in vacuo
8. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1-1:2)

ORD record

ord-046a03c62c3e4d919b8347f8c4ccb248

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09101616B2