反应 #2314348

反应方程式

diethyl 2-{[(5-iodo-6-methyl-2-pyridinyl)amino]methylene}malonate

ethanol

→

product

收率 52.0%

Ethyl 4-hydroxy-6-iodo-7-methyl[1,8]naphthyridine-3-carboxylate

收率 52.0%

溶剂

diphenyl ether

—

Hexanes

反应条件

后处理

1. 1
   过滤the solid is filtered
2. 2
   洗涤washed thoroughly with hexanes
3. 3
   其他dried
4. 4
   workup.DISSOLUTIONThe crude solid is dissolved in CH2Cl2/MeOH
5. 5
   其他Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L))

实验过程

A solution of diethyl 2-{[(5-iodo-6-methyl-2-pyridinyl)amino]methylene}malonate Prep 3(1.09 g) in 20 mL diphenyl ether is heated at 250° C. for 2 h with removal of ethanol via a Dean-Stark trap. The reaction is cooled to room temperature. Hexanes (15 mL) are added and the solid is filtered, washed thoroughly with hexanes, and dried. The crude solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L)) affords the product as a yellow-green solid (0.50 g, 52%). Physical characteristics are as follows: m.p. 275-277° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 12.80, 8.72, 8.47, 4.21, 2.74, 1.27; IR (drift) 2981, 1718, 1606, 1524, 1407, 1376, 1356, 1319, 1291, 1244, 1192, 1185, 1109, 809, 623 cm−1; MS (ESI) m/z 358.9 (M+H)+, 356.9 (M−H)−; Anal. Calcd for C12H11IN2O3: C, 40.24; H, 3.10; N, 7.82; Found: C, 40.15; H, 3.05; N, 7.81.

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