反应详情

Typical procedure to prepare 2-cyanoquinoline from N-oxide: Preparation of 2-cyano-5-hydroxyl-2-quinoline: Trimethylsilyl cyanide (12.4 ml) was added into a solution of 5-hydroxyl-quinoline N-oxide (5 g) with triethylamine (13 ml) in MeCN. After the reaction was stirred at room temperature for 12 hours, solvents were removed under vaccum to provide a residue which was then partitioned between saturated NaHCO3 solution (100 ml) and EtOAc (100 ml). The aqueous solution was then extracted with EtOAc (2×100 ml). And the combined organic layer was dried over anhydrous MgSO4, filtered and concentrated to afford a crude product which purified by silica gel column chromatography to provide 5.3 g of 2-cyano-5-hydroxylquinoline. MS m/z: (M+H)+ calcd for C10H7N2O 171.06, found 171.03. HPLC retention time: 1.22 minutes (column I).

1. customsolvents were removed under vaccum
2. customto provide a residue which
3. customwas then partitioned between saturated NaHCO3 solution (100 ml) and EtOAc (100 ml)
4. extractionThe aqueous solution was then extracted with EtOAc (2×100 ml)
5. dry with materialAnd the combined organic layer was dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford a crude product which
9. custompurified by silica gel column chromatography