2(1H)-Quinoxalinone → 7-bromo-1H-quinoxalin-2-one

HRID 1019966Notes

Reaction equation

HRID 1019966 reaction equation
[Br:1]Br.[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]1=[O:13]>C(O)(=O)C>[Br:1][C:10]1[CH:11]=[C:12]2[C:7]([N:6]=[CH:5][C:4](=[O:13])[NH:3]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 145262(1H)-QuinoxalinoneHCID 24408Bromine

Product 1

HCID 49132647-bromo-1H-quinoxalin-2-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (7.36 mL, 147 mmol, 1.05 eq) is added at room temperature to a stirred suspension of 1H-quinoxalin-2-one (20 g, 137 mmol, 1.0 eq) in acetic acid (400 mL). After 48 hours stirring at room temperature, the reaction mixture is poured into ice (500 mL) and the resulting precipitate is collected by filtration, washed with water and ethyl acetate to afford 7-bromo-1H-quinoxalin-2-one as a yellow solid (29.4 g, 73% yield).

Workup

  1. filtrationthe resulting precipitate is collected by filtration
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-2f860a95fd20407cbfb8020aff68371d
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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