Water → HCID 86732660, compound

HRID 523447Notes

Reaction equation

HRID 523447 reaction equation
[C:1]1([N:7]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:29])C(=O)C1.O>C(Cl)Cl.C(#N)C>[Br:29][C:4]1[CH:3]=[CH:2][C:1]([N:7]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 3179895-Phenylphenanthridin-6(5H)-one

Product 1

HCID 86732660HCID 86732660, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6.0 g (22 2 mmol) of 5-phenyl-5H-phenanthridin-6-one are initially introduced in 150 ml of CH2Cl2. A solution of 4 g (22 5 mmol) of NBS in 100 ml of acetonitrile is subsequently added dropwise at −15° C. with exclusion of light, 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: 7.4 g (21 mmol), 80% of theory, purity according to 1H-NMR about 96%.

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-7d9655b9d04a46d7937d88da132e2347
Source dataset
uspto-grants-2016_05
Patent number
US09337430B2

Reaction notes

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