Phenylhydrazine → 6-Phenyl-8-(3-nitrophenyl) pyrido[2,3-d]pyridazin-5-one

HRID 861952Notes

Reaction equation

HRID 861952 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=[CH:11][N:10]=1)=O)([O-:3])=[O:2].[C:22]1([NH:28][NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[C:22]1([N:28]2[C:15](=[O:17])[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]=3[C:7]([C:6]3[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 197007162-(3-Nitrobenzoyl)-3-methoxycarbonylpyridine

Product 1

HCID 538506476-Phenyl-8-(3-nitrophenyl) pyrido[2,3-d]pyridazin-5-oneYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3-nitrobenzoyl)-3-methoxycarbonylpyridine (0.26 g, 0.97 mmoles) dissolved in ethanol (50 ml), was added phenylhydrazine (0.25 ml, 2.4 mmoles). The mixture was refluxed for 168 hours. The solvent was removed and the solid was precipitated from ethanol and dried, yielding 0.07 g of 6-phenyl-8-(3-nitrophenyl) pyrido[2,3-d]pyridazin-5-one (21%), mp 167° C.

Workup

  1. temperatureThe mixture was refluxed for 168 hours
  2. customThe solvent was removed
  3. customthe solid was precipitated from ethanol
  4. customdried

Sources & evidence

ORD record
ord-8f0f0911f84c4fb081874095f8476667
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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