Water → 6-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

HRID 1627746Notes

Reaction equation

HRID 1627746 reaction equation
[CH3:1][C:2]1([CH3:22])[C:15]2[C:10]3=[C:11]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[CH:13][CH:14]=2.C1C(=O)N([Br:30])C(=O)C1.O>C(Cl)Cl.C(#N)C>[Br:30][C:13]1[CH:14]=[C:15]2[C:10]3=[C:11]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:2]2([CH3:22])[CH3:1])[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 125554028,8-dimethyl-8H-indolo[3,2,1-de]acridine

Product 1

HCID 671097356-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6.3 g (22.2 mmol) of 8,8-dimethylindolo[3,2,1-de]acridine are initially introduced in 150 ml of CH2Cl2. A solution of 8 g (45.1 mmol) of NBS in 100 ml of acetonitrile is subsequently added dropwise at −15° C. with exclusion of light, and the mixture is allowed to come to room temperature and is stirred at this temperature for a further 4 h. 150 ml of water are subsequently added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvents are removed in vacuo. The product is washed by stirring with hot hexane and filtered off with suction. Yield: 4.5 g (12 mmol), 57% of theory, purity according to 1H-NMR about 97%.

Workup

  1. customto come to room temperature
  2. extractionis then extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvents are removed in vacuo
  5. washThe product is washed
  6. stirringby stirring with hot hexane
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-b1e5fb8dd18d4714a5f950853e05ce8b
Source dataset
uspto-grants-2014_07
Patent number
US08785636B2

Reaction notes

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