Pyruvic Acid → 1-ethyl-3-methylquinoxalin-2(1H)-one

HRID 76365Notes

Reaction equation

HRID 76365 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:10])=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].O=[C:12]([CH3:16])[C:13](O)=[O:14]>CO>[CH2:1]([N:3]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:10]=[C:12]([CH3:16])[C:13]1=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 1060Pyruvic AcidHCID 902751,2-Benzenediamine, N1-ethyl-

Product 1

HCID 129004081-ethyl-3-methylquinoxalin-2(1H)-oneYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.4 g (39.6 mM) of N-ethylbenzene-1,2-diamine and 2.76 ml (39.6 mM) of 2-oxopropanoic acid in 200 ml of methanol were refluxed for 8 h. The solvent was removed under vacuum. The residue was further purified by silica gel column chromatography, using dichloromethane, followed by dichloromethane/dimethylketone (95/5) as eluant to give 4.2 g of 1-ethyl-3-methyl-quinoxalin-2(1H)-one as a yellow solid. Yield: 56.7%.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-771cc522ad1d4d8f9471e1362b965d8d
Source dataset
uspto-grants-2014_09
Patent number
US08835634B2

Reaction notes

Loading…