2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

HRID 400460Notes

Reaction equation

HRID 400460 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2=[N:29][N:30]([CH3:34])[C:31](=[O:33])[CH2:32][CH:25]2[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2=[N:29][N:30]([CH3:34])[C:31](=[O:33])[CH:32]=[C:25]2[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11430Potassium CarbonateHCID 866860582-Methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

Product 1

HCID 866860592-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl esterYield 52.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3 g DDQ was added to 2.5 g 2-methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester in 25 mL dioxane. The reaction was refluxed for 12 h. Then aqueous potassium carbonate solution was added and the mixture was extracted with chloroform. The organic layer was washed with brine. The crude product was purified by column chromatography on silica gel to yield 1.3 g of the desired product.

Workup

  1. temperatureThe reaction was refluxed for 12 h
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3d7c3baae2f74170bb803737c9f5c040
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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