Glyoxal → 5,8-Dibromoquinoxaline
Reaction equation
[CH:1]([CH:3]=O)=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8]([NH2:13])[C:7]=1[NH2:14]>CCO>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8]2[C:7]=1[N:14]=[CH:1][CH:3]=[N:13]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 40% aqueous solution of glyoxal (8.8 M, 6.3 mL, 55.1 mmol, 1.3 equiv) was added to a suspension of 3,6-dibromo-benzene-1,2-diamine (Step 1.6) (11.3 g, 42.4 mmol) in EtOH (280 mL). The reaction mixture was heated to reflux for 3 h and allowed to cool to rt overnight. Vacuum filtration of the reaction mixture afforded 9.7 g of the title compound as a yellow solid: APCI-MS: 286.2/288.1/290.1 [M−1]−; tR=4.40 min (System 1).
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux for 3 h
- filtrationVacuum filtration of the reaction mixture
Sources & evidence
- ORD record
- ord-3752f261596140a6bdbe69df656e39c9
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536175B2
Reaction notes
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