Benzoyl Peroxide → 7-(Bromomethyl)-1-chloroisoquinoline

HRID 651590Notes

Reaction equation

HRID 651590 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([CH3:38])[CH:36]=2)[CH:31]=[CH:30][N:29]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][CH2:38][C:35]1[CH:36]=[C:37]2[C:32]([CH:31]=[CH:30][N:29]=[C:28]2[Cl:27])=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 222501861-Chloro-7-methylisoquinoline

Product 1

HCID 181762527-(Bromomethyl)-1-chloroisoquinolineYield 97%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (1.10 g, 6.19 mmol) and benzoyl peroxide (0.39 g, 1.13 mmol) are added to a solution of 1-chloro-7-methylisoquinoline (1 g, 5.63 mmol) in carbon tetrachloride (70 mL). The resulting mixture is heated to reflux for 6 hours then cooled to room temperature and diluted with methylene chloride. The organic layer is washed with 1N NaOH and brine, then dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 25% EtOAc/hexanes to give the product (1.4 g, 5.46 mmol) as a white solid.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 6 hours
  3. washThe organic layer is washed with 1N NaOH and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography
  8. washeluting with a gradient of 10% EtOAc/hexanes to 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-9c9c8ccb31944cb0b0fcfb80493d89d5
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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