Selenium Dioxide → Quinazoline-6-carbaldehyde

HRID 1783613Notes

Reaction equation

HRID 1783613 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[CH:5]2.[Se](=O)=[O:13]>CO>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:13])=[CH:11][CH:10]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 152205446-Methylquinazoline

Product 1

HCID 22060156Quinazoline-6-carbaldehydeYield 43.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 6-methyl-quinazoline (5.0 g, 34.7 mmol) and selenium dioxide (7.7 g, 69.4 mmol) was heated at 160° C. for 12 hours. After cooling to room temperature, methanol was added with stirring. After removal of solid by filtration, the filtrate was concentrated. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-30% ethyl acetate in hexane in 30 min) afforded 6-quinazolinecarboxaldehyde (2.4 g, 43.7%) as a white solid: LC-MS m/e 159 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. customAfter removal of solid
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4932d407f85c4531818eec34895cacb4
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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