Toluene → 6,7-Dichloroquinoxalin-2(1H)-one

HRID 2114326Notes

Reaction equation

HRID 2114326 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](OCC)(=O)[CH:12]=[O:13].C1(C)C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[NH:9][C:12](=[O:13])[CH:11]=[N:10]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 144236366,7-Dichloroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Dichlorophenylenediamine (26.0 g, 147 mmol) and 50% ethyl glyoxylate in toluene (32 mL, 161 mmol) in ethanol (250 mL) was refluxed for 18 h. The reaction was cooled and the crystallized brown product was collected by filtration, then washed with ethanol (50 mL). The obtained product (25.5 g, 81%) was 96% pure via LC/MS. MS (ES) m/e 215[M+H]+.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe crystallized brown product was collected by filtration
  3. washwashed with ethanol (50 mL)

Sources & evidence

ORD record
ord-a74fd23f4cc340d3b24782ce4189fc46
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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