Acetic Anhydride → 1-Acetamido-1,4-dihydro-2,3-quinoxalinedione

HRID 53734Notes

Reaction equation

HRID 53734 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]1=[O:13].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([NH:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]1=[O:13])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 220972261-Amino-1,4-dihydro-2,3-quinoxalinedione

Product 1

HCID 199585641-Acetamido-1,4-dihydro-2,3-quinoxalinedioneYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-amino-1,4-dihydro-2,3-quinoxalinedione (53 mg, 0.30 mMol) and pyridine (1 mL, fresh distilled from KOH before use) and acetic anhydride (1 mL, Aldrich) was stirred under nitrogen at 60° C. for 4 hrs. The reaction mixture became a clear solution. All of solvent and reagent were then evaporated under reduced pressure and washed with benzene:cyclohexane=1:1(2×2 mL); ether (2×2 mL), dried at 60° C. with rotavapor for 2 h, affording 57 mg (86%) of pure 1-acetamido-1,4-dihydro-2,3-quinoxalinedione as a white powder; mp: 211°-213° C. IR (KBr, cm-1): 3430; 3127; 1741; 1717; 1668. NMR (1H, DMSO-d6) δ 2.326 (s, 3H); 7.121-7.287 (m, 4H); 12.345 (s, 1H). Mass:calcd for C10H9N3O3 (M+) m/z:219.0641; found: 219.0651.

Workup

  1. customAll of solvent and reagent were then evaporated under reduced pressure
  2. washwashed with benzene
  3. dry with materialether (2×2 mL), dried at 60° C. with rotavapor for 2 h

Sources & evidence

ORD record
ord-1adda79f88d8432a91959ae85e9a3023
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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