Acetic Acid → Quinoxaline

HRID 895157Notes

Reaction equation

HRID 895157 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](O)(=O)[CH3:10].CCOCC>C1(C)C=CC=CC=1>[N:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 7243O-Phenylenediamine

Product 1

HCID 7045Quinoxaline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2-phenylenediamine (2.3 g) and acetic acid (1 ml) were added to a solution of the compound mentioned above (7.54 g) in toluene (50 ml), and the mixture was heated under reflux for an hour. The solid formed upon addition of ether to the reaction mixture at 0° C. was filtered to give a quinoxaline derivative (1.91 g). The compound was dissolved in tetrahydrofuran (500 ml), and sodium hydride (60%, 1.0 g) and 2-trimethylsilylethoxymethyl chloride (8.6 ml) were added to the solution at room temperature. The mixture was stirred for an hour. Aqueous ammonium chloride was added to the reaction mixture, and then extracted with ethyl acetate. The organic layer was washed with water and aqueous ammonium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a compound protected by the SEM group.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for an hour
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-013838f52d854ed083393498e161225a
Source dataset
uspto-grants-2005_07
Patent number
US06914062B2

Reaction notes

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