反应详情

Lithium borohydride (434 mg, 19.93 mmol) is added to a suspension of 7-benzyloxy-5-(2-chloroacetyl)-1H-quinolin-2-one (6 g, 18.31 mmol) in THF (150 mL) at 0° C.-5° C. and the mixture is stirred for 30 minutes. 2.5 N sodium hydroxide solution (43 mL, 107.50 mmol) is added and the mixture is stirred for 2 hours at 5° C.-10° C. and for 2.5 hours at ambient temperature. Then the reaction mixture is slowly combined with glacial acetic acid (6.5 mL) followed by semisaturated sodium chloride solution (100 mL) and stirred for a further 5 minutes. The precipitate formed is filtered off and the aqueous phase is extracted with ethyl acetate/THF (1/1.5×100 mL). The solid filtered off and the organic phases are combined, dried with sodium sulfate, and evaporated down. The crude product is stirred with methanol (30 mL) and the precipitate is filtered off and dried at ambient temperature. Yield: 4.8 g (89%); mass spectroscopy: [M+H]+=294.

1. stirringthe mixture is stirred for 2 hours at 5° C.-10° C. and for 2.5 hours at ambient temperature
2. stirringstirred for a further 5 minutes
3. customThe precipitate formed
4. filtrationis filtered off
5. extractionthe aqueous phase is extracted with ethyl acetate/THF (1/1.5×100 mL)
6. filtrationThe solid filtered off
7. dry with materialdried with sodium sulfate
8. customevaporated down
9. stirringThe crude product is stirred with methanol (30 mL)
10. filtrationthe precipitate is filtered off
11. customdried at ambient temperature