Ethyl Acetate → 2-Oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate

To a solution of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (3.456 g, 21.18 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added potassium carbonate (4.146 g, 30.00 mmol), then and trifluoromethanesulfonyl chloride (5.000 g, 29.67 mmol) in N,N-dimethylformamide (5 mL) dropwise. The reaction mixture was stirred at room temperature for 24 hours, and a second portion of potassium carbonate (4.146 g, 30.00 mmol) and trifluoromethanesulfonyl chloride (5.000 g, 29.67 mmol) in N,N-dimethylformamide (5 was added slowly, and stirred for 16 hours. Evaporation of the solvent under reduced pressure gave a crude mixture to which a mixture of 15% ethyl acetate in n-hexane (20 mL) and water (50 mL) was added. Diethyl ether (5 mL) was added and the mixture sonicated, filtered, and the solid thus obtained was washed with 3M aqueous potassium carbonate (100 mL), water (200 mL), n-hexane (100 mL), 15% ethyl acetate in n-hexane (30 mL), and dried to afford 2-oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate as a yellow solid (4.311 g, 14.60 mmol, 69%). LCMS mz 295.9 (M+H), 317.9 (M+Na), anal HPLC >90% in purity, 1H NMR (400 MHz; CDCl3) δ8.17 (bs, 1H); 7.23 (d, J=8.2 Hz, 1H); 6.90 (dd, J=8.2 and 2.3 Hz, 1H); 6.71 (d, J=2.3 Hz, 1H); 3.00 (m, 2H); 2.67 (m, 2H).

1. stirringstirred for 16 hours
2. customEvaporation of the solvent under reduced pressure
3. customgave a crude mixture to which
4. additionwas added
5. customthe mixture sonicated
6. filtrationfiltered
7. customthe solid thus obtained
8. washwas washed with 3M aqueous potassium carbonate (100 mL), water (200 mL), n-hexane (100 mL), 15% ethyl acetate in n-hexane (30 mL)
9. customdried

ORD record

ord-06578100e6974e55ab7e268222d7998b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952007B2