O-Phenylenediamine → Ethyl 3-hydroxyquinoxaline-2-carboxylate

HRID 2269731Notes

Reaction equation

HRID 2269731 reaction equation
O=[C:2]([C:8]([O:10]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19]>C(O)C>[O:10]=[C:8]1[NH:20][C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:19]=[C:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 691051,3-Diethyl 2-oxopropanedioate

Product 1

HCID 248643Ethyl 3-hydroxyquinoxaline-2-carboxylateYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Diethyl ketomalonate (8 g) was added to an ethanol (100 ml) solution of 1,2-phenylenediamine (5 g). The reaction mixture was stirred at 50° C. for 14 hours. The precipitated crystals were filtrated, which was washed with IPE to obtain the entitled compound (8.2 g).

Workup

  1. filtrationThe precipitated crystals were filtrated
  2. washwhich was washed with IPE

Sources & evidence

ORD record
ord-01d7a3f0a0164db1b73957bdbb1646d4
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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