Pyridine → 2,6-Di-tert-butyl-4-[(pyrazin-2-yl)imino]cyclohexa-2,5-dien-1-one

HRID 345763Notes

Reaction equation

HRID 345763 reaction equation
N1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:11]([C:15]1[C:16](=[O:26])[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:19](=O)[CH:20]=1)([CH3:14])([CH3:13])[CH3:12].[NH2:27][C:28]1[CH:33]=[N:32][CH:31]=[CH:30][N:29]=1>ClC(Cl)C>[C:11]([C:15]1[C:16](=[O:26])[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:19](=[N:27][C:28]2[CH:33]=[N:32][CH:31]=[CH:30][N:29]=2)[CH:20]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 128672,6-Di-t-butyl-p-benzoquinoneHCID 78747AminopyrazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 143736662,6-Di-tert-butyl-4-[(pyrazin-2-yl)imino]cyclohexa-2,5-dien-1-oneYield 58.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A 1.62 ml quantity of pyridine was dissolved in 60 ml of dichloroethane. To the solution was added 0.89 g of aluminum chloride powder, and the mixture was refluxed with heating for 15 minutes. Then to the mixture were added 2.20 g of 2,6-di-tert-butyl-1,4-benzoquinone and 0.95 g of aminopyrazine, and the mixture was refluxed under heating for 17.5 hours. The reaction mixture was cooled to room temperature and filtered through a Celite pad and the insoluble materials were washed there with dicloromethane. The filtrate was concentrated, and the resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=3:7), giving 1.73 g of Compound 1a.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 15 minutes
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 17.5 hours
  5. filtrationfiltered through a Celite pad
  6. washthe insoluble materials were washed there with dicloromethane
  7. concentrationThe filtrate was concentrated
  8. customthe resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=3:7)

Sources & evidence

ORD record
ord-3dd159d9b0b8427183d52d987c187d70
Source dataset
uspto-grants-1991_10
Patent number
US05059598

Reaction notes

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