4-cyano-3-methylisoquinoline → 3-(Bromomethyl)-4-isoquinolinecarbonitrile

HRID 1726948Notes

Reaction equation

HRID 1726948 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]#[N:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]#[N:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 17334-cyano-3-methylisoquinolineHCID 67184N-bromobutanimide

Product 1

HCID 574997723-(Bromomethyl)-4-isoquinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

39 mg azo-isobutyronitrile are added to a boiling mixture of 400 mg 3-methyl-4-cyano-isoquinoline and 440 mg N-bromosuccinimide in 30 ml carbon tetrachloride. The reaction mixture is refluxed for two hours. After cooling to ambient temperature the precipitate formed is suction filtered and washed with carbon tetrachloride. The filtrate is evaporated down and chromatographed through a silica gel column with methylene chloride as eluant.

Workup

  1. temperatureThe reaction mixture is refluxed for two hours
  2. customformed
  3. filtrationfiltered
  4. washwashed with carbon tetrachloride
  5. customThe filtrate is evaporated down
  6. customchromatographed through a silica gel column with methylene chloride as eluant

Sources & evidence

ORD record
ord-f7a5864a6eba44459338f66efb97bc74
Source dataset
uspto-grants-2009_02
Patent number
US07495002B2

Reaction notes

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