Cyclohexane → 1-(3,4-Dimethoxy-phenyl)-4-hydroxy-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester

HRID 1818697Notes

Reaction equation

HRID 1818697 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4](=[N:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[C:5](=[O:11])[CH2:6][C:7](OC)=[O:8].C1CCCCC1>C1C(Cl)=CC=C(Cl)C=1>[CH3:1][O:2][C:3]([C:4]1[C:5]([OH:11])=[CH:6][C:7](=[O:8])[N:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[N:12]=1)=[O:24]

Participants

4

Reactant 2

HCID 8078CyclohexaneHCID 178500931HCID 178500931, compound

Product 1

HCID 578861981-(3,4-Dimethoxy-phenyl)-4-hydroxy-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl esterYield 65.2%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

The hydrazone (28) (500 mg) was dissolved in dichlorobenzene and heated to reflux in a sealed tube for 4 hours. The reaction was allowed to cool and cyclohexane was added dropwise to crystallize the desired product. Filtration and drying in vacuo yielded the desired dihydropyridazine ester (29) (295 mg) as a solid. MS+: m/e=307.0 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux in a sealed tube for 4 hours
  3. temperatureto cool
  4. customto crystallize the desired product
  5. filtrationFiltration
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-76b1633605fd47dd85330c48c70f5914
Source dataset
uspto-grants-2009_10
Patent number
US07601718B2

Reaction notes

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