N,N-Dimethylaniline → 9-Chlorophenanthridine

HRID 467385Notes

Reaction equation

HRID 467385 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C1C=CC=CC=1.[CH:15]1[C:28]2[C:19](=[N:20][CH:21]=[C:22]3[C:27]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:18]=[CH:17][CH:16]=1>O>[Cl:3][C:25]1[CH:24]=[CH:23][C:22]2[C:27]([CH:26]=1)=[C:28]1[C:19]([CH:18]=[CH:17][CH:16]=[CH:15]1)=[N:20][CH:21]=2

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 9189PhenanthridineHCID 24813Phosphorus oxychloride

Product 1

HCID 673172599-ChlorophenanthridineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (15 ml) and dimethylaniline (0.63 ml) were added to phenanthridine (2.0 g), followed by refluxing for 3 hours. The solution was poured into H2O to generate a solid, and the obtained solid was extracted with chloroform, followed by drying with sodium sulfate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The obtained solid was purified by column chromatography (eluent: chloroform) (amount: 2.1 g, yield: 96%).

Workup

  1. temperatureby refluxing for 3 hours
  2. extractionthe obtained solid was extracted with chloroform
  3. dry with materialby drying with sodium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customThe obtained solid was purified by column chromatography (eluent: chloroform) (amount: 2.1 g, yield: 96%)

Sources & evidence

ORD record
ord-efba66156385427dbe80e4808b229765
Source dataset
uspto-grants-2014_01
Patent number
US08623239B2

Reaction notes

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