Pyridine → 3-Bromo-6-quinolinecarbonitrile

HRID 902569Notes

Reaction equation

HRID 902569 reaction equation
[Br:1]Br.N1C=CC=CC=1.[C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[CH:14]2)#[N:10]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:15]1[CH:16]=[N:17][C:18]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:9]#[N:10])=[CH:20][CH:19]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 592995Quinoline-6-carbonitrile

Product 1

HCID 181862093-Bromo-6-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In an amount of 37.8 mg of 6-cyanoquinoline (Justus Liebigs Ann. Chem., 1966, 699, 98-106) was dissolved in 1 ml of carbon tetrachloride, added with 13 μl of bromine, and then stirred under reflux. After 2 hours, the reaction mixture was added with 20 μl of pyridine, and further stirred for 23 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (4:1)) to obtain 34.8 mg of the title compound.

Workup

  1. temperatureunder reflux
  2. stirringfurther stirred for 23 hours
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (4:1))

Sources & evidence

ORD record
ord-f178da4f9adc49b598327e4d0468bb40
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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