Selenium Dioxide → 2-Phenyl-quinoline-8-aldehyde

HRID 2372823Notes

Reaction equation

HRID 2372823 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7]2.[Se](=O)=[O:19]>C(Cl)Cl>[C:12]1([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:2]([CH:1]=[O:19])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24007Selenium Dioxide2×HCID 140689928-Methyl-2-phenylquinoline

Product 1

HCID 151703302-Phenyl-quinoline-8-aldehydeYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

8.46 g of 8-methyl-2-phenylquinoline [compare Atwell, G.J. et al., J. Med. Chem. 32, 396-401 (1989)] are mixed with 8.9 g (80 mmol) of selenium dioxide and heated first to 140° C. with stirring, then to 160° C. for 5 hours. The mixture is cooled, a further 2.5 g of selenium dioxide are added and the mixture is stirred at 160° C. for 2.5 hours. It is cooled, stirred with methylene chloride, the solid is filtered off and the filtrate is concentrated. The mixture obtained is purified by flash chromatography on silica gel using toluene/hexane 1:1 and toluene. 3.9 g of beige colored crystals of melting point 100°-102° C. are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. stirringthe mixture is stirred at 160° C. for 2.5 hours
  3. temperatureIt is cooled
  4. filtrationthe solid is filtered off
  5. concentrationthe filtrate is concentrated
  6. customThe mixture obtained
  7. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a6e74addbf0544b7a5cc3f93d8701e17
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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