Phenacyl bromide → Quinoxaline

HRID 2389252Notes

Reaction equation

HRID 2389252 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].CCN(C(C)C)C(C)C>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 81531Diisopropylethylamine

Product 1

HCID 7045Quinoxaline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of the appropriate α-bromoacetophenone (1 eq) in 5 ml of ethanol was added the appropriate 1,2-phenylenediamine (2.7 eq), followed by DIPEA (3.4 eq). The resultant solution was stirred at room temperature overnight with an air atmosphere. The reaction was concentrated, then purified by reverse phase chromatography on a C-18 column using a 0 to 90% gradient of CH3CN in water, with both containing 0.05% TFA. Product containing fractions were lyophilized to give a powder.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reverse phase chromatography on a C-18 column
  3. additionProduct containing fractions
  4. customto give a powder

Sources & evidence

ORD record
ord-21942672486345f8ac1ca8ebd13f72d5
Source dataset
uspto-grants-2012_09
Patent number
US08273743B2

Reaction notes

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