Ethanol → 1-(3,4-Dihydroquinoxalin-1(2h)-yl)ethanone

HRID 1515347Notes

Reaction equation

HRID 1515347 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.[CH2:11]([OH:13])[CH3:12]>C(OC(=O)C)(=O)C.[OH-].[Na+]>[C:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 702EthanolHCID 770281,2,3,4-Tetrahydroquinoxaline

Product 1

HCID 2415071-(3,4-Dihydroquinoxalin-1(2h)-yl)ethanone

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroquinoxaline obtained in Reference Example 26 (360 mg) in ethanol (10 ml), acetic anhydride (254 μl) was added dropwise under ice cooling and stirred at room temperature for 10 minutes. The reaction mixture was diluted with 1M aqueous sodium hydroxide (10 ml) and extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was distilled off under reduced pressure to give the titled compound, i.e., 1-acetyl-1,2,3,4-tetrahydroquinoxaline (494 mg) as a brown oil.

Workup

  1. additionwas added dropwise under ice cooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a3fe6206b0324603b0201b52ce20cac5
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

Loading…