Cyclohexanone → HCID 11287987, compound

HRID 1070466Notes

Reaction equation

HRID 1070466 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([C:9]#[N:10])[C:7]([NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[NH2:10][C:9]1[C:8]2[C:7]([N:12]=[C:13]3[C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18]3)=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=2

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 11287987HCID 11287987, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-nitroanthranilonitrile (1.63 g, 10 mmol) and cyclohexanone (10.3 ml, 100 mmol) was added zinc chloride (1.36 g, 10 mmol) and the mixture was refluxed under heating for 20 min. The reaction mixture was cooled to room temperature and diluted with ethyl acetate, and the insoluble matter was filtered off. The filtrate was concentrated under reduced pressure and chloroform was added to the obtained brown oil. The resulting yellow precipitate was collected by filtration and dried under reduced pressure at 80° C. This solid (1.56 g) was diluted with ethyl acetate and 1N aqueous sodium hydroxide solution, and ether was added. The insoluble matter was collected by filtration and dried under reduced pressure at 80° C. to give 9-amino-7-nitro-1,2,3,4-tetrahydroacridine (810 mg, 33%) as a yellow solid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 20 min
  3. filtrationthe insoluble matter was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure and chloroform
  5. additionwas added to the obtained brown oil
  6. filtrationThe resulting yellow precipitate was collected by filtration
  7. customdried under reduced pressure at 80° C
  8. additionThis solid (1.56 g) was diluted with ethyl acetate and 1N aqueous sodium hydroxide solution, and ether
  9. additionwas added
  10. filtrationThe insoluble matter was collected by filtration
  11. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-3f9fe9ef97c645bdb08078fed664f74d
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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