Dichloromethane → Trifluoromethanesulfonic acid 6,7-dimethoxyquinolin-4-yl ester

To a dry 1 L RBF containing 6,7-dimethoxy-quinolin-4-ol (20.9 g, 102 mmol), which can be prepared according to the procedure of Riegel, B. (J. Amer. Chem. Soc. 1946, 68, 1264), was added DCM (500 mL), 4-dimethylaminopyridine (1.24 g, 10 mmol) and 2,6-lutidine (24 mL, 204 mmol). The mixture was vigorously stirred at RT. Trifluoromethanesulfonyl chloride (14 mL, 132 mmol) was added dropwise to the solution. After addition was complete, the mixture was stirred ice bath for 2 to 3 hrs. On LC/MS indicating the reaction completion, the reaction mixture was concentrated in vacuo and placed under high vacuum to remove residual 2,6-lutidine. To the resulting brown solids was added methanol (250 mL). The resulting slurry was stirred for 30 min before adding water (1 L). The solids were isolated by filtration, followed by a water wash. The resulting solid was dried under high vacuum overnight yielding trifluoromethanesulfonic acid 6,7-dimethoxy-quinolin-4-yl ester as a light brown solid (27 g, 80%). 1H NMR (400 MHz, DMSO, d6): δ 8.82 (d, 1H), 7.59 (m, 2H), 7.20 (s, 1H), 3.97 (d, 6H). LC/MS: M+H=338.

1. customcan be prepared
2. additionAfter addition
3. stirringthe mixture was stirred ice bath for 2 to 3 hrs
4. concentrationthe reaction mixture was concentrated in vacuo
5. customto remove residual 2,6-lutidine
6. additionTo the resulting brown solids was added methanol (250 mL)
7. stirringThe resulting slurry was stirred for 30 min
8. additionbefore adding water (1 L)
9. customThe solids were isolated by filtration
10. washwash
11. customThe resulting solid was dried under high vacuum overnight

ORD record

ord-ff0cb84daf3f4155a6440369fd20c774

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476298B2