Réaction #3213

Équation de réaction

dimethyl 4-aminoquinoline-2,3-dicarboxylate

hydrazine hydrate

→

title compound

Rendement 98.8%

10-Amino-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione

Rendement 98.8%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurethe resulting solution was refluxed for 3 hr
2. 2
   Filtrationfiltered
3. 3
   Autreto separate the yellow precipitate (0.12 g)
4. 4
   Températurein refluxing acetic acid (4.5 mL) for 1 hr
5. 5
   TempératureAfter cooling to room temperature the reaction mixture
6. 6
   Filtrationwas filtered
7. 7
   Lavagethe collected solids washed with acetic acid and ethyl acetate
8. 8
   AutreAir drying

Mode opératoire

To a stirred solution of dimethyl 4-aminoquinoline-2,3-dicarboxylate (0.15 g, 0.58 mM) in ethanol (4 mL) was added hydrazine hydrate (1.46 g, 29.2 mM) and the resulting solution was refluxed for 3 hr. The reaction mixture was cooled to room temperature and filtered to separate the yellow precipitate (0.12 g). This material was stirred in refluxing acetic acid (4.5 mL) for 1 hr. After cooling to room temperature the reaction mixture was filtered and the collected solids washed with acetic acid and ethyl acetate. Air drying provided the title compound (0.13 g, 68%) as an orange solid, mp>400° C.; MS(CI): 229 (M+H).

Source