Oxalyl chloride → 1-Ethyl-3-hydroxyquinoxalin-2(1H)-one
Reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:10])=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13]>CO>[CH2:1]([N:3]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:12](=[O:13])[C:11]1=[O:15])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To 12 g (88.1 mmol) of N-ethylbenzene-1,2-diamine in 150 ml of methanol were added dropwise 8.1 g (92.5 mM) of oxalyl chloride. The exothermic mixture reached 55° C. and solidified. The mixture was heated at 130° C. for 2 h. The purple solid formed was filtered and washed with isopropanol to give 1-ethyl-1,4-dihydroquinoxaline-2,3-dione as a solid (7.2 g). Yield: 43%.
Workup
- customreached 55° C.
- customThe purple solid formed
- filtrationwas filtered
- washwashed with isopropanol
Sources & evidence
- ORD record
- ord-751d312a8c82408198f172ab8cb0f61c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415352B2
Reaction notes
Loading…