Hydrogen Peroxide → 8-Bromoquinoxalin-2(1H)-one

HRID 216727Notes

Reaction equation

HRID 216727 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][NH:7]2.C(OC(=O)CNC1C=CC=C(Br)C=1N)C.[OH-].[Na+].OO>Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[N:7]2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 593926768-bromo-3,4-dihydro-1H-quinoxalin-2-oneHCID 59392693Ethyl 2-(2-amino-3-bromophenylamino)acetate

Product 1

HCID 593927088-Bromoquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

A sealable tube is charged with 4.99 g (39.549 mmol) of a mixture of 8-Bromo-3,4-dihydro-1H-quinoxalin-2-one with (2-Amino-3-bromo-phenylamino)-acetic acid ethyl ester (as obtained in step 1.2). 50 mL of a 1M NaOH solution and 12.1 ml of a 30% H2O2 aqueous solution are added. The tube is sealed and heated to 95° C. for 1 h. After cooling, 50 mL of 1M HCl solution are added slowly and the brown solid is collected by filtration, to afford, after drying in HV at 50° C., the title compound which is used without further purification.

Workup

  1. customThe tube is sealed
  2. temperatureAfter cooling
  3. filtrationthe brown solid is collected by filtration
  4. customto afford
  5. customafter drying in HV at 50° C.
  6. customthe title compound which is used without further purification

Sources & evidence

ORD record
ord-d8622136d6464ed5bb3b10b017170c8c
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

Loading…