반응 #3219

반응 방정식

diethyl oxosuccinate sodium salt

8-chloro-2H-3,1-benzoxazine-2,4(1H)-dione

water

→

solid

수율 43.8%

Diethyl 8-chloro-4-hydroxyquinoline-2,3-dicarboxylate

수율 43.8%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도maintained at this temperature for 2.5 hr
2. 2
   온도After cooling
3. 3
   추출the resulting mixture was then extracted with ethyl acetate
4. 4
   세척The combined organic extracts were washed with water and brine
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

To a stirred mixture of diethyl oxosuccinate sodium salt (2.31 g, 11.0 mM) in dimethylformamide (20 mL) under a nitrogen atmosphere was added 8-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (2.17 g, 11.0 mM). The resulting mixture was heated slowly to 130° C. and maintained at this temperature for 2.5 hr. After cooling, the reaction mixture was poured into water and the resulting mixture was then extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated to obtain an oily solid (1.55 g). This material was chromatographed (eluant: CH2C12 /CH3OH; 98/2) over silica gel to provide the title compound as an oil which slowly crystallized to a tan solid (0.700 g, 19.7%). A 0.150 g portion of this material was recrystallized from toluene/hexane to provide an analytical sample (0.050 g) of the title compound as a tan solid, mp 98°-99° C.; MS(CI): 324 (M+H).

출처