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

HRID 1422801Notes

Reaction equation

HRID 1422801 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-8716d3ed1fcd43aaa717e0f6dbbd5b5a
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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