Acetic Acid → 5,8-Dibromo-2,3-diphenylquinoxaline

HRID 1912212

Reaction equation

HRID 1912212 reaction equation
[Br:1][C:2]1[C:3]([NH2:10])=[C:4]([NH2:9])[C:5]([Br:8])=[CH:6][CH:7]=1.C(O)(=O)C.[C:15]1([C:21]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[C:4]2[C:3]=1[N:10]=[C:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[N:9]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8651BenzilHCID 516892Sodium BicarbonateHCID 118215323,6-Dibromobenzene-1,2-diamine

Product 1

HCID 224759015,8-Dibromo-2,3-diphenylquinoxalineYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Preparation procedure: 3,6-dibromo-o-phenylene diamine (1.0 g, 3.7 mmol) is added to an acetic acid (20 mL) solution of benzil (0.39 g, 1.84 mmol) at 120° C. The resulting solution is mixed homogeneously and reflux for 12 hours. The reaction solution is poured into water, neutralized with sodium bicarbonate, extracted with chloroform, washed with saturated brine water, and dried over anhydrous sodium sulfate. The solvents are removed using a rotary evaporator. The crude product is subjected to column chromatography to give a white solid, which is then recrystallized in chloroform/n-hexane to afford a white solid powder (yield 86%), MALDI-TOF-MS (m/z): 440.1 (M+).

Workup

  1. customPreparation procedure
  2. additionThe resulting solution is mixed homogeneously
  3. temperaturereflux for 12 hours
  4. extractionextracted with chloroform
  5. washwashed with saturated brine water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvents are removed
  8. customa rotary evaporator
  9. customto give a white solid, which
  10. customis then recrystallized in chloroform/n-hexane

Sources & evidence

ORD record
ord-f2dc75123a7d4ef98313fa61a8cd868e
Source dataset
uspto-grants-2013_12
Patent number
US08604147B2

Linked notes

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