반응 #3195

반응 방정식

dimethyl 4-hydroxyquinoline-2,3-dicarboxylate

hydrazine hydrate

→

hydrazine

수율 112.8%

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

수율 112.8%

용매

ethanol

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   온도The resulting solution was refluxed for 3 hr during which time a thick precipitate
3. 3
   기타formed
4. 4
   기타The cooled reaction mixture
5. 5
   여과was filtered
6. 6
   세척the collected yellow solids were washed with ethanol
7. 7
   기타Air drying

실험 절차

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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