2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23471598, compound

HRID 128019Notes

Reaction equation

HRID 128019 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][CH2:11]3)=[N:6][NH:5][C:4](=[O:20])[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[CH:11]3)=[N:6][NH:5][C:4](=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 129826Y 590

Product 1

HCID 23471598HCID 23471598, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.4 g of 6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1-methyl-1,2,3,4-tetrahydroquinolin-2-one, 5.5 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 500 ml of benzene was heated under reflux for 48 hours. After cooling, the precipitated crystals were filtered off. The filtrate was washed with a 10% sodium hydroxide solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue and the crystals were combined and purified by using a column chromatograph. The resulting crystals were recrystallized from methanol to give 1.5 g of 6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1-methyl-1,2-dihydroquinolin-2-one, melting at 248°-251° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered off
  5. washThe filtrate was washed with a 10% sodium hydroxide solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. custompurified
  9. customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-23aebc49575048f78dc97f67179657f2
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

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