Acetic Acid → 6-Iodoquinoxaline

HRID 1661829Notes

Reaction equation

HRID 1661829 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.

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-70563e14deb54e779a5d2ba26d101122
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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