N-bromobutanimide → 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

HRID 985151Notes

Reaction equation

HRID 985151 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH3:15])=[C:6]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:15][C:7]1[N:8]([CH3:14])[C:9](=[O:13])[C:10]2[C:5]([C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 225559912,3-dimethyl-6-methoxy4-phenyl-2H-isoquinolin-1-one

Product 1

HCID 225559473-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 12 (3.08 g, 11.0 mmol) in carbon tetrachloride under Argon was added N-bromosuccinimide (1.96 g, 11.0 mmol). The contents of the reaction flask were heated to reflux. After 3 h an additional portion of N-bromosuccinimide (0.50 g, 2.81 mmol) was added to the reaction flask. After 7 h the solvent was removed in vacuo and sat. sodium bicarbonate was added. Extracted with methylene chloride (4×) and dried the combined organic portions with magnesium sulfate (anh.). Removal of the solvent in vacuo followed by trituration with ether gave 13 as a light solid (3.47 g, 9.70 mmol, 88.2%)

Workup

  1. temperatureThe contents of the reaction flask were heated to reflux
  2. customAfter 7 h the solvent was removed in vacuo and sat. sodium bicarbonate
  3. additionwas added
  4. extractionExtracted with methylene chloride (4×)
  5. dry with materialdried the combined organic portions with magnesium sulfate (anh.)
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-451ffba0cf3043e4ba1863900689913d
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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