N-bromobutanimide → 3-(Bromomethyl)isoquinolin-1(2H)-one

HRID 868906Notes

Reaction equation

HRID 868906 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C1C=CC(C2C=CC(C3OC(C4C=CC=CC=4)=CN=3)=CC=2)=CC=1.[Br:36]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:36][CH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 967282-(Biphenyl-4-yl)-5-phenyloxazoleHCID 32444773-Methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 700972123-(Bromomethyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a refluxing solution of 3-methylisoquinolin-1(2H)-one (1.7 g, 10.69 mmol) and 2-(4-biphenyl)-5-phenyloxazole (120 mg) in CCl4 (30 mL) was added N-bromosuccinimide (1.9 g, 10.7 mmol) in portions. The reaction mixture was stirred at reflux for 2 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc, filtered and concentrated to give the crude product, which was used for the next step without further purification. LC-MS: m/z 238 (M+H+).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea588e2b03f5477e8066257f1a425e14
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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