Methyl iodide → 7-Methoxyquinoline

Temperature

0 °C

A suspension of NaH (3.3 g; 137.93 mmol) in anhydrous DMF (160 ml) was cooled to 0° C. with stirring under argon. 7-Quinolinol (8 g; 55.17 mmol) dissolved in anhydrous DMF (320 ml) was added and the mixture was stirred at 0° C. under argon for 1 h. The mixture was then allowed to warm to rt and MeI (7.8 ml; 55.17 mmol) was added and the reaction was stirred for 1 h. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3×500 ml). The organic layer from this extraction was then washed with water (400 ml) and brine (400 ml). The resulting organic layer was dried with MgSO4 and solvents removed to afford the desired compound (8.76 g; 99%)

1. additionwas added
2. stirringthe mixture was stirred at 0° C. under argon for 1 h
3. temperatureto warm to rt
4. stirringthe reaction was stirred for 1 h
5. extractionthe resulting mixture extracted with EtOAc (3×500 ml)
6. extractionThe organic layer from this extraction
7. washwas then washed with water (400 ml) and brine (400 ml)
8. dry with materialThe resulting organic layer was dried with MgSO4 and solvents
9. customremoved

ORD record

ord-2a9506de2aac4e4f8738396daa2562aa

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071592B2