Acetic Acid → 6-Iodoquinoxaline

HRID 1921653Notes

Reaction equation

HRID 1921653 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10](=O)[CH:11]=O.C(O)(=O)C.C(O)C>O>[I:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:11][CH:10]=[N:9]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 7860GlyoxalHCID 112070494-Iodobenzene-1,2-diamine

Product 1

HCID 242717656-IodoquinoxalineYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-iodo-benzene-1,2-diamine (0.46 g, 1.96 mmol), ethanedial [40% in water] (2.25 mL), acetic acid (1 mL) and ethanol (20 mL) were heated to 100° C. for several hours and then cooled to room temperature. Water was added and the crude product was extracted with ethyl acetate. The product was purified via silica gel column chromatography with hexane:ethyl acetate (1:1) to give 0.323 g (64%) of 6-iodo-quinoxaline. 1H NMR (400 MHz, CDCl3) δ 8.77 (dd, 2H, J=2.0, 8.8 Hz), 8.46 (d, 1H, 2.0 Hz), 7.96 (dd, 1H, J=2.0, 8.8 Hz), 7.75 (d, 1H, J=8.8 Hz).

Workup

  1. extractionthe crude product was extracted with ethyl acetate
  2. customThe product was purified via silica gel column chromatography with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7df8e814b7ac4beba5ebb624bc524a3b
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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