反应详情

7-Methylquinoline (1-1, 240 g, 1.7 mol, 1.0 equiv) was dissolved in methylene chloride (5 L, 0.34 M). 3-Chloroperoxybenzoic acid (488 g, 2.2 mol, 1.3 equiv) was added portionwise with cooling so that the reaction temperature did not rise above 34° C. After stirring for 1 h, the reaction mixture was quenched with 2 L of 1N aqueous NaOH and the product was extracted with methylene chloride. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried over MgSO4 and filtered. Heptane was added and the organic layer was evaporated to dryness, giving 246 g of 7-methylquinoline N-oxide (1-2) as a pink solid that was carried on without further purification. LRMS m/z (M+H)+ 160.1 found, 160.2 required.

1. temperaturewith cooling so that the reaction temperature
2. customdid not rise above 34° C
3. customthe reaction mixture was quenched with 2 L of 1N aqueous NaOH
4. extractionthe product was extracted with methylene chloride
5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. additionHeptane was added
9. customthe organic layer was evaporated to dryness