N-bromobutanimide → 3-(bromomethyl)-1-ethyl-quinoxalin-2(1H)-one

HRID 76366Notes

Reaction equation

HRID 76366 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[C:4]1=[O:14])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.COC(C)(C)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:13][C:5]1[C:4](=[O:14])[N:3]([CH2:1][CH3:2])[C:12]2[C:7]([N:6]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 129004081-ethyl-3-methylquinoxalin-2(1H)-one

Product 1

HCID 581109593-(bromomethyl)-1-ethyl-quinoxalin-2(1H)-oneYield 40.3%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4.2 g (22.3 mM) of 1-ethyl-3-methyl-quinoxalin-2(1H)-one, 3.97 g (22.3 mM) of N-bromosuccinimide and 53.3 mg of benzoylperoxide in 220 ml of carbon tetrachloride were refluxed for 4 h. The reaction mixture was filtered and the solvent was removed under vacuum. The residue was further purified by silica gel column chromatography, using dichloromethane/cyclohexane (70/30) as eluant to give a solid, which was taken up in methylterbutyloxide. After filtration, 2.4 g of 3-(bromomethyl)-1-ethyl-quinoxalin-2(1H)-one were obtained as a tan solid. Yield: 40.3%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum
  3. customThe residue was further purified by silica gel column chromatography
  4. customto give a solid, which
  5. filtrationAfter filtration

Sources & evidence

ORD record
ord-8e2cf00c212e4ca9b1c3baa180395d01
Source dataset
uspto-grants-2014_09
Patent number
US08835634B2

Reaction notes

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