反応 #3195

反応方程式

dimethyl 4-hydroxyquinoline-2,3-dicarboxylate

hydrazine hydrate

→

hydrazine

収率 112.8%

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

収率 112.8%

溶媒

ethanol

反応条件

後処理

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

実験手順

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).

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