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

HRID 929343Notes

Reaction equation

HRID 929343 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]1=[O:11].[Br:12]Br>CC(O)=O>[Br:12][C:8]1[CH:9]=[C:10]2[C:5]([N:4]=[CH:3][C:2](=[O:11])[NH:1]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 145262(1H)-QuinoxalinoneHCID 24408Bromine

Product 1

HCID 49132647-bromo-1H-quinoxalin-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of quinoxalin-2(1H)-one (54.64 g, 374 mmol, 1.0 eq.) in HOAc (1000 mL) was added a solution of Br2 (19.18 mL, 374 mmol, 1.0 eq.) in HOAc (200 mL) dropwise. The resulting mixture was stirred at rt for 12 h, then poured into ice-water. The precipitate was collected by filtration and dried to afford 7-bromoquinoxalin-2(1H)-one as an off-white solid (74 g, 88%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-3be1c1469e544e20b90065f85dcbb030
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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