Phenacyl bromide → Quinoxaline

HRID 2389257Notes

Reaction equation

HRID 2389257 reaction equation
BrCC([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11]1([NH2:18])C=CC=C[C:12]=1[NH2:17].C([O-])(=O)C.[Na+]>C(O)C>[N:17]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:18]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 7243O-PhenylenediamineHCID 517045Sodium Acetate

Product 1

HCID 7045Quinoxaline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of the appropriate alpha-bromoacetophenone (1 eq) in 200 ml of ethanol was added the appropriate 1,2-phenylenediamine (2.4 eq), followed by addition of solid sodium acetate (3 eq). The resultant solution was warmed to reflux and stirred overnight with an air atmosphere. The product formed precipitates, and so the reaction was vacuum filtered, and the solids washed with 50 ml cold ethanol followed by washing with 50 ml 0.1 N HCl. The product was carried on without further purification.

Workup

  1. temperatureto reflux
  2. customThe product formed
  3. customprecipitates
  4. filtrationfiltered
  5. washthe solids washed with 50 ml cold ethanol
  6. washby washing with 50 ml 0.1 N HCl
  7. customThe product was carried on without further purification

Sources & evidence

ORD record
ord-0a62b9bcab0d499c86348edcdeb1bf20
Source dataset
uspto-grants-2012_09
Patent number
US08273743B2

Reaction notes

Loading…