O-Phenylenediamine → 3-Aminoquinoxalin-2(1H)-one

HRID 235299Notes

Reaction equation

HRID 235299 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([O:14]CC)(=S)[C:10]([NH2:12])=O>C(O)C>[NH2:12][C:10]1[C:9](=[O:14])[NH:7][C:2]2[C:1]([N:8]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 216137632-ethoxy-2-thioxoAcetamide

Product 1

HCID 47380403-Aminoquinoxalin-2(1H)-oneYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

An adaptation of the method of Burrell et al., J. Chem. Soc. Perkin I. 2707 (1973), was used. A mixture of 1,2-phenylenediamine (324 mg, 3.00 mmol; Aldrich Co.) and ethyl thiooxamate (400 mg, 3.00 mmol; Aldrich Co.) in 7.5 mL of ethanol was heated to reflux. The resulting solution was stirred under reflux for 3 h. The resulting suspension was cool to 25° C. A pale yellow precipitate appeared. The mixture was vacuum filtered and the solid was washed with EtOH (5×2 mL) and dried in vacuum at 60° C. overnight to yield 85 mg (18%) of 3-aminoquinoxalin-2(1H)-one as a pale yellow solid (McKillop et al., Tetrahedron Lett. 23:3357 (1982)): mp dec.>320° C. 1H NMR (300 MHz, DMSO-d6) δ 7.261-7.075 (m, 4H, H-5+H-6+H-7+H-8). LRMS: 161 (M+, 100%), 133 (50%).

Workup

  1. temperaturewas heated to reflux
  2. temperatureunder reflux for 3 h
  3. filtrationfiltered
  4. washthe solid was washed with EtOH (5×2 mL)
  5. customdried in vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-3d74b713e29c4316b19d0c96a0e2d235
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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