Nitrogen → 2-Chloro-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

HRID 628219Notes

Reaction equation

HRID 628219 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:22]=[CH:21][C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1.N#N.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O>[Cl:8][C:9]1[CH:22]=[CH:21][C:20]2[N:19]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 11575IodobenzeneHCID 227542562-Chloro-9,9-dimethyl-9,10-dihydroacridineHCID 23676156Sodium t-butoxide

Product 1

HCID 668032642-Chloro-9,9-dimethyl-10-phenyl-9,10-dihydroacridineYield 81.9%

Reagents, catalysts & solvents 4

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A degassed solution of 16.6 ml (147 mmol) of 4-iodobenzene and 30 g (123 mmol) of 2-chloro-9,9-dimethyl-9,10-dihydroacridine in 600 ml of toluene is saturated with N2 for 1 h. Then, firstly 2.09 ml (8.6 mmol) of P(tBu)3, then 1.38 g (6.1 mmol) of palladium(II) acetate are added, and subsequently 17.7 g (185 mmol) of NaOtBu in the solid state are added to the solution. the reaction mixture is heated under reflux for 1 h. After the mixture has been cooled to room temperature, 500 ml of water are carefully added. The aqueous phase is washed with 3×50 ml of toluene and dried over MgSO4, and the solvent is removed in vacuo. Filtration of the crude product through silica gel with heptane/ethyl acetate (20:1) gives 32.2 g (81%) of 2-chloro-9,9-dimethyl-10-phenyl-9,10-dihydroacridine as pale-yellow crystals.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 1 h
  3. washThe aqueous phase is washed with 3×50 ml of toluene
  4. dry with materialdried over MgSO4
  5. customthe solvent is removed in vacuo
  6. filtrationFiltration of the crude product through silica gel with heptane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-59f312c48b2d46f1b955c021082c3690
Source dataset
uspto-grants-2016_04
Patent number
US09312495B2

Reaction notes

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