Hydrochloric Acid → 8-Bromoquinoxalin-2(1H)-one

HRID 1056029Notes

Reaction equation

HRID 1056029 reaction equation
OO.[NH2:3][C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][CH2:12][C:13]([O:15]CC)=O.[OH-].[Na+].Cl>>[Br:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:3][C:13](=[O:15])[CH:12]=[N:11]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 59392693Ethyl 2-(2-amino-3-bromophenylamino)acetate

Product 1

HCID 593927088-Bromoquinoxalin-2(1H)-oneYield 38%

Conditions

Temperature
95 °C

Procedure

30% H2O2 (14.27 ml, 466 mmol) was added to a mixture of ethyl 2-((2-amino-3-bromophenyl)amino)acetate (12.72 g, 46.6 mmol) in 1 N aq. NaOH (58.2 ml, 58.2 mmol) before it was heated to 95° C. for 2 h in a sealed tube behind a blast shield. After cooling the reaction, 1 N HCl (58 ml) was added, and the precipitated solid was filtered, washed with water, and dried in a vacuum oven (50° C., over the 3 d) to give 8-bromoquinoxalin-2(1H)-one (210d, 38% yield over two steps) as a brown solid. MS (ESI, pos. ion) m/z: 225.0/227.0 (M+1).

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried in a vacuum oven (50° C.

Sources & evidence

ORD record
ord-351b22ad2d114b4780cb6e4cc6e884c7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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