Selenium Dioxide → Beta-Carboline

HRID 1619482Notes

Reaction equation

HRID 1619482 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3](C(OCC)=O)[NH:2]1.[Se](=O)=O>C(O)(=O)C>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 650777HCID 650777, compound

Product 1

HCID 64961Beta-CarbolineYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 10b (24.4 g, 0.1 mol) was mixed with glacial acetic acid (500 ml) followed by the addition of selenium dioxide (20 g, 0.2 mol). The mixture was refluxed for 12 h. The glacial acetic acid was removed I. 1M NaOH solution (200 ml) was added into the residues, then the mixture was extracted with ethyl acetate. The organic phases were combined, washed by 1M NaOH solution, water and brine, dried, decolorized with activated carbon, filtered, evaporated and recrystallized with ethyl acetate to afford white solids (10.0 g, 60%), and mp 197-198° C. (reference[20]: 198 to 200° C.).

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. customThe glacial acetic acid was removed I
  3. addition1M NaOH solution (200 ml) was added into the residues
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed by 1M NaOH solution, water and brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customrecrystallized with ethyl acetate

Sources & evidence

ORD record
ord-5e4757161c7743e688e0e9f0eee9f2ef
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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