6-Methylquinoline → 6-Quinolinecarbaldehyde

HRID 907996Notes

Reaction equation

HRID 907996 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.CC[O:14]C(C)=O>>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 70596-MethylquinolineHCID 8857Ethyl Acetate

Product 1

HCID 7656536-QuinolinecarbaldehydeYield 20%

Conditions

Temperature
150 °C

Procedure

A mixture of SeO2 (10.89 g, 99 mmol) and 6-methylquinoline (12.87 g, 90 mmol) was heated to 150° C. and stirred for 16 h. Then it was cooled to room temperature and EtOAc (400 ml) was added. After filtration, the filtrate was concentrated to obtain the crude compound, which was purified by chromatography (silica gel, petroleum ether/EtOAc 5:1 to 2:1) to afford the title compound (2.87 g, yield 20%). LC-MS (ESI) m/z: 158 (M+1)+.

Workup

  1. temperatureThen it was cooled to room temperature
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated
  4. customto obtain the crude compound, which
  5. customwas purified by chromatography (silica gel, petroleum ether/EtOAc 5:1 to 2:1)

Sources & evidence

ORD record
ord-8c2e024319264d8f977392c3c7a3e39d
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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