Selenium Dioxide → 6-Phenanthridinecarboxaldehyde

HRID 1975251Notes

Reaction equation

HRID 1975251 reaction equation
OC[CH:3]([C:6]1[N:7]=[C:8]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][CH:10]=[CH:9]2)CO.[Se](=O)=[O:21]>C(OCC)(=O)C>[CH:3]([C:6]1[N:7]=[C:8]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][CH:10]=[CH:9]2)=[O:21]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 19097762HCID 19097762, compound

Product 1

HCID 2898346-PhenanthridinecarboxaldehydeYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In the next step, a mixture of 6-(2-hydroxy-1-hydroxymethyl)-phenanthridine (24) (6 g, 31 mmoles) and finely powdered selenium dioxide (3.8 g, 34 mmoles) is refluxed in ethyl acetate (125 ml) for 10 hours. The deep red solution that form is then filtered while hot through celite, before evaporating to dryness. The resulting solid is digested in warm 1M hydrochloric acid (125 ml), filtered and partially neutralized with sodium bicarbonate. The initial red precipitate is filtered off before completely neutralizing the solution. The resulting pale yellow solid is filtered off and recrystallized from acetone/petroleum ether to give 2.7 g of 6-formylphenanthridine (yield=42%).

Workup

  1. filtrationThe deep red solution that form is then filtered while hot through celite
  2. custombefore evaporating to dryness
  3. filtrationfiltered
  4. filtrationThe initial red precipitate is filtered off
  5. filtrationThe resulting pale yellow solid is filtered off
  6. customrecrystallized from acetone/petroleum ether

Sources & evidence

ORD record
ord-66e7d5ba565b40d8ac9eae6ac4d67235
Source dataset
uspto-grants-1994_02
Patent number
US05284951

Reaction notes

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