Hydrazine hydrate (1:1) → HCID 178418284, compound

HRID 1451292Notes

Reaction equation

HRID 1451292 reaction equation
[OH: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>[OH: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 178418327HCID 178418327, compound

Product 1

HCID 178418284HCID 178418284, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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). Analysis for C11H7N3O3 : Calculated: C, 57.65; H, 3.08; N, 18.33 Found: C, 57.54; H, 3.26; N, 18.64

Workup

  1. dissolutiondissolved
  2. temperatureThe resulting solution was refluxed for 3 hr during which time a thick precipitate
  3. customformed
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. washthe collected yellow solids were washed with ethanol
  7. customAir drying

Sources & evidence

ORD record
ord-00bfa08341ab40e49ea216e546623425
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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