反应 #3195

反应方程式

dimethyl 4-hydroxyquinoline-2,3-dicarboxylate

hydrazine hydrate

→

hydrazine

收率 112.8%

2,3-Dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione

收率 112.8%

溶剂

ethanol

反应条件

后处理

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   温度The resulting solution was refluxed for 3 hr during which time a thick precipitate
3. 3
   其他formed
4. 4
   其他The cooled reaction mixture
5. 5
   过滤was filtered
6. 6
   洗涤the collected yellow solids were washed with ethanol
7. 7
   其他Air drying

实验过程

To a stirred suspension of dimethyl 4-hydroxyquinoline-2,3-dicarboxylate (1.00 g, 3.83 mM, prepared as described by H. Biere and W. Seelen, Liebigs Ann. Chem. 1976, 1972) in ethanol (15 mL) was added hydrazine hydrate (9.64 g, 193 mM) whereupon the solids dissolved. The resulting solution was refluxed for 3 hr during which time a thick precipitate formed. The cooled reaction mixture was filtered and the collected yellow solids were washed with ethanol and then ether. Air drying provided 0.99 g of the hydrazine salt of 2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione. This material was boiled in glacial acetic acid (40 mL) and, after cooling to room temperature, the mixture was filtered. The collected solids were washed with several portions of ethyl acetate and then ether. Air drying provided the title pyridazinodione (0.72 g, 82%) as a yellow solid, mp>400° C.; Mass Spectrum (Chemical Ionization): 230 (M+H).

来源