2-Chloroaniline → 2-Chlorophenyl-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)amine

HRID 1485596Notes

Reaction equation

HRID 1485596 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([CH3:23])([CH3:22])[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:4]=2[CH:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:2]1[CH:7]=[CH:6][C:5]2[N:8]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:15]([CH3:23])([CH3:22])[C:14]4[C:9]3=[C:10]([CH:11]=[CH:12][CH:13]=4)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 72402-ChloroanilineHCID 23676156Sodium t-butoxideHCID 671095853-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Product 1

HCID 674515792-Chlorophenyl-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)amine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

66.2 g (183 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine (Br-1), 28 g (220 mmol) of 2-chlorophenylamine, 1.5 g of DPPF (2.7 mmol), 0.5 g of palladium(II) acetate and 45 g of sodium tert-butoxide (486 mmol) are heated at the boil in 1.5 l of toluene for 18 h under a protective atmosphere. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator. The residue remaining is recrystallised from heptane/ethyl acetate. The yield is 43 g (107 mmol, 59%).

Workup

  1. customThe mixture is subsequently partitioned between toluene and water
  2. washthe organic phase is washed three times with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in a rotary evaporator
  5. customThe residue remaining is recrystallised from heptane/ethyl acetate

Sources & evidence

ORD record
ord-a089d1626df84b34aaaeeb7da4c07f54
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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