Water → 7-Chloro-1-hydroxy-3-(4-chlorophenyl)-3,4,5,10-tetrahydropyridazino[4,5-b]quinoline-4,10-dione

HRID 1600037Notes

Reaction equation

HRID 1600037 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18]C)=O)[C:8]([C:12]([O:14]C)=O)=[N:9]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1.C(N(CC)CC)C.O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:16]([OH:18])=[N:29][N:28]([C:25]4[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=4)[C:12](=[O:14])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70624(4-Chlorophenyl)hydrazineHCID 178418477HCID 178418477, compound

Product 1

HCID 1785150727-Chloro-1-hydroxy-3-(4-chlorophenyl)-3,4,5,10-tetrahydropyridazino[4,5-b]quinoline-4,10-dioneYield 37.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.50 g, 8.45 mM) and 4-chlorophenyl hydrazine (10.60 g, 59.20 mM) in ethanol (50 mL) was added triethylamine (9.43 mL) to give a brown solution. This solution was refluxed for 24 hours and then cooled to room temperature. Dilution with water (25 mL) gave a brown precipitate. This suspension was stirred for 16hours and filtered to remove the solids which were discarded. The filtrate formed another precipitate after standing for seven days. This solid was collected and washed with aqueous methanol (50%) and ether to give the 4-chlorophenyl hydrazine salt of the title compound as a brown powder (1.20 g). This material was refluxed in glacial acetic acid (25 mL) for 3 hours and cooled to room temperature. The resulting orange suspension was filtered, and the solids were washed with glacial acetic acid and ether togive the title compound (0.810 g, 25%) as a light orange powder, mp 399°-401° C.; MS(CI): 374 (M+H).

Workup

  1. customto give a brown solution
  2. temperatureThis solution was refluxed for 24 hours
  3. filtrationfiltered
  4. customto remove the solids which
  5. customThe filtrate formed another precipitate
  6. waitafter standing for seven days
  7. customThis solid was collected
  8. washwashed with aqueous methanol (50%) and ether

Sources & evidence

ORD record
ord-0e493d80d4ae4f0eb813f713c5f05de9
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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