Hydrazine hydrate (1:1) → 10-Amino-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione

HRID 1451300Notes

Reaction equation

HRID 1451300 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12](OC)=[O:13])[C:3]=1[C:16]([O:18]C)=O.O.[NH2:21][NH2:22]>C(O)C>[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[C:12](=[O:13])[NH:21][NH:22][C:16](=[O:18])[C:3]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18929891Dimethyl 4-aminoquinoline-2,3-dicarboxylate

Product 1

HCID 1536492810-Amino-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dioneYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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). Analysis for C11H8N4O2 ·1.7 CH3CO2H: Calculated: C, 52.36; H, 4.52; N, 16.96 Found: C, 52.26; H, 4.55; N, 16.90

Workup

  1. temperaturethe resulting solution was refluxed for 3 hr
  2. filtrationfiltered
  3. customto separate the yellow precipitate (0.12 g)
  4. temperaturein refluxing acetic acid (4.5 mL) for 1 hr
  5. temperatureAfter cooling to room temperature the reaction mixture
  6. filtrationwas filtered
  7. washthe collected solids washed with acetic acid and ethyl acetate
  8. customAir drying

Sources & evidence

ORD record
ord-a2121d66c8de4e539b0a9942528ad745
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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