Methanesulfonic Acid → 2-Chloro-9,9-dimethyl-9,10-dihydroacridine

HRID 628218Notes

Reaction equation

HRID 628218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15](O)([CH3:17])[CH3:16])=[CH:4][CH:3]=1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:15]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 668033732-[2-(4-Chlorophenylamino)phenyl]propan-2-ol

Product 1

HCID 227542562-Chloro-9,9-dimethyl-9,10-dihydroacridineYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30.3 g (116 mmol) of 2-[2-(4-chlorophenylamino)phenyl]propan-2-ol are dissolved in 700 ml of degassed toluene, a suspension of 93 g of polyphosphoric acid and 61.7 g of methanesulfonic acid is added, and the mixture is stirred at room temperature for 1 h and heated at 50° C. for 1 h. The batch is cooled, added to ice and extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. Filtration of the crude product through silica gel with heptane/ethyl acetate (20:1) gives 25.1 g (89%) of 2-chloro-9,9-dimethyl-9,10-dihydroacridine as pale-yellow crystals.

Workup

  1. additionis added
  2. temperatureheated at 50° C. for 1 h
  3. temperatureThe batch is cooled
  4. additionadded to ice
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic phases are washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. filtrationFiltration of the crude product through silica gel with heptane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-569413cc31024cc6b844be7d851ebc04
Source dataset
uspto-grants-2016_04
Patent number
US09312495B2

Reaction notes

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