Methylhydrazine → 6-Methylpyrido[2,3-d]pyridazin-5(6H)-one

HRID 1291218Notes

Reaction equation

HRID 1291218 reaction equation
[CH:1]([C:3]1[C:8]([C:9]([O:11]CC)=O)=[CH:7][CH:6]=[CH:5][N:4]=1)=O.[CH3:14][NH:15][NH2:16]>C(O)C>[CH3:14][N:15]1[C:9](=[O:11])[C:8]2[CH:7]=[CH:6][CH:5]=[N:4][C:3]=2[CH:1]=[N:16]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 15639417Ethyl 2-formylnicotinate

Product 1

HCID 189191106-Methylpyrido[2,3-d]pyridazin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (3 ml) was dissolved ethyl 2-formyl-3-pyridinecarboxylate (519 mg) followed by addition of methylhydrazine (267 mg), and the mixture was refluxed with stirring for 2 hours. This reaction mixtrue was concentrated to dryness and the residue was washed with diethyl ether-acetone and dried. Yellow powder, 391 mg. 1H-NMR (DMSO-d6) δ: 3.75(3H,s), 7.86(1H,dd,J=8.4&4.4Hz), 8.48(1H,s), 8.62(1H,d,J=8.4Hz), 9.14(1H,d,J=4.4Hz).

Workup

  1. temperaturethe mixture was refluxed
  2. customThis reaction
  3. concentrationmixtrue was concentrated to dryness
  4. washthe residue was washed with diethyl ether-acetone
  5. customdried

Sources & evidence

ORD record
ord-47fa0c3bffa94f23b511decafbf1729e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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