Acetic Anhydride → HCID 23273816, compound

HRID 1772006Notes

Reaction equation

HRID 1772006 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2378596-Quinoxalinamine

Product 1

HCID 23273816HCID 23273816, compoundYield 47%

Procedure

A solution of quinoxalin-6-amine (14.0 g, 0.97 mol) in acetic anhydride (120 mL) was stirred at 100° C. for 1 h. Excess acetic anhydride was removed under reduced pressure. To the residue was added 150 mL of saturated aqueous sodium bicarbonate solution. The mixture was extracted with DCM (3×150 mL), and the combined organic layers were dried over sodium sulfate and concentrated under reduce pressure to give N-(quinoxalin-6-yl)acetamide as a yellow solid (8.4 g, yield 47%). ESI MS: m/z 188.1 [M+H]+.

Workup

  1. customExcess acetic anhydride was removed under reduced pressure
  2. additionTo the residue was added 150 mL of saturated aqueous sodium bicarbonate solution
  3. extractionThe mixture was extracted with DCM (3×150 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9e87e1618d748a2aba448ac651b445f
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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