Oxalyl chloride → 1-Ethyl-3-hydroxyquinoxalin-2(1H)-one

HRID 1961561Notes

Reaction equation

HRID 1961561 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

HCID 65578Oxalyl chlorideHCID 902751,2-Benzenediamine, N1-ethyl-

Product 1

HCID 144605371-Ethyl-3-hydroxyquinoxalin-2(1H)-oneYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customreached 55° C.
  2. customThe purple solid formed
  3. filtrationwas filtered
  4. washwashed with isopropanol

Sources & evidence

ORD record
ord-751d312a8c82408198f172ab8cb0f61c
Source dataset
uspto-grants-2013_04
Patent number
US08415352B2

Reaction notes

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