反应 #3212

反应方程式

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

sodium formate

water

→

solid

收率 134.8%

Dimethyl 7-chloroquinoline-2,3-dicarboxylate

收率 134.8%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度was heated at 90°-95° C. for 7 hr
2. 2
   其他was degassed
3. 3
   workup.ADDITIONan additional quantity of tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) was added
4. 4
   温度the reaction mixture again heated at 90°-95° C. for 6 hr
5. 5
   其他The cooled reaction mixture
6. 6
   萃取the resulting mixture extracted with ethyl acetate
7. 7
   干燥The combined extracts were dried (MgSO4)
8. 8
   过滤filtered
9. 9
   浓缩concentrated

实验过程

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).

来源