Benzoyl Peroxide → 3-(Bromomethyl)-1-methyl-1,2-dihydroquinoxalin-2-one

HRID 2051649Notes

Reaction equation

HRID 2051649 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([CH3:38])[C:29]1=[O:39]>C(Cl)(Cl)(Cl)Cl>[CH3:27][N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([CH2:38][Br:1])[C:29]1=[O:39]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3514221,3-dimethylquinoxalin-2(1H)-one

Product 1

HCID 2528873-(Bromomethyl)-1-methyl-1,2-dihydroquinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (3.36 g., 0.0189 mol.) and benzoyl peroxide (0.06 g.) were added to a solution of 1,3-dimethyl-2(1H)-quinoxalinone (3.0 g., 0.017 mol.) in carbon tetrachloride (250 ml.). The mixture was heated at reflux for four hours. Removal of the solvent left a tan solid. Chromatography on silica gel with methylenechloride as the eluent gave a tan solid. Recrystallization from methylene chloride gave light tan needles. (2.33 g., m.p. 192.5-193.5°. 53%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for four hours
  3. customRemoval of the solvent
  4. waitleft a tan solid
  5. customChromatography on silica gel with methylenechloride as the eluent gave a tan solid
  6. customRecrystallization from methylene chloride
  7. customgave light tan needles

Sources & evidence

ORD record
ord-0f274617df6b4799919a78a090b8f7a6
Source dataset
uspto-grants-1980_01
Patent number
US04181724

Reaction notes

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