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

HRID 323620
Notes
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Reaction equation

HRID 323620 reaction equation
CO[C:3]([C:5]1[C:14]([C:15]([O:17]C)=O)=[C:13]([OH:19])[C:12]2[C:7](=[CH:8][C:9]([Cl:20])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[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:20][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[O:19])[C:14]3[C:15]([OH:17])=[N:29][N:28]([C:25]4[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=4)[C:3](=[O:4])[C:5]=3[NH:6][C:7]=2[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 702
Ethanol
Solvent

Procedure

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.50 g, 8.45 mM) and 4-chlorophenylhydrazine (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 16 hours 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-chlorophenylhydrazine 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 to give 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-ccc049cf5a694efd8cba87cf9eeaff82
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214826B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes