Acetic Anhydride → HCID 23273816, compound

HRID 1615640Notes

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

Reactant 2

HCID 7918Acetic Anhydride

HCID 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

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

Sources & evidence

ORD record: ord-1f1fde0ce672480d9a901829c34c3ced
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765760B2

Reaction notes

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