O-Phenylenediamine → Methyl (3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)acetate

HRID 1642141Notes

Reaction equation

HRID 1642141 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](OCC)(=[O:17])/[CH:10]=[CH:11]\[C:12]([O:14][CH2:15]C)=[O:13]>C(O)CC>[O:17]=[C:9]1[NH:8][C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:7][CH:10]1[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 5271566Diethyl Maleate

Product 1

HCID 21027845Methyl (3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Orthophenylenediamine (10 g, 92.4 mmol) and diethyl maleate (45 g, 646.8 mmol) were refluxed for 75 h in propanol. The solvent was removed using a rotary evaporator and the residue was purified by column chromatography (ethyl acetate/hexane 1:1).

Workup

  1. customThe solvent was removed
  2. customa rotary evaporator
  3. customthe residue was purified by column chromatography (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-0f075b1158374d678740c17b3e90ed28
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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