반응 #3212

반응 방정식

dimethyl 4,7-dichloroquinoline-2,3-dicarboxylate

sodium formate

water

→

solid

수율 134.8%

Dimethyl 7-chloroquinoline-2,3-dicarboxylate

수율 134.8%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도was heated at 90°-95° C. for 7 hr
2. 2
   기타was degassed
3. 3
   workup.ADDITIONan additional quantity of tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) was added
4. 4
   온도the reaction mixture again heated at 90°-95° C. for 6 hr
5. 5
   기타The cooled reaction mixture
6. 6
   추출the resulting mixture extracted with ethyl acetate
7. 7
   건조The combined extracts were dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

A stirred mixture of dimethyl 4,7-dichloroquinoline-2,3-dicarboxylate (5.00 g, 15.9 mM), sodium formate (1.63 g, 23.9 mM) and tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) in anhydrous dimethylformamide (75 mL) under a nitrogen atmosphere was heated at 90°-95° C. for 7 hr. No reaction occurred so the reaction mixture was degassed and an additional quantity of tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) was added and the reaction mixture again heated at 90°-95° C. for 6 hr. The cooled reaction mixture was poured into water and the resulting mixture extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and concentrated to leave an gummy solid (6.0 g). Trituration of this residue with ethyl acetate and subsequent filtration separated a crystalline solid which was shown to be dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate. The filtrate was concentrated and the residue was flash chromatographed over silica gel (eluant: hexane/ethyl acetate, 3/2) to provide the title diester (1.13 g, 25.4%) as a light yellow crystalline solid; MS(CI): 280 (M+H).

출처