6-Methylquinoline → 6-Quinolinecarbaldehyde

HRID 1968114Notes

Reaction equation

HRID 1968114 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-9f12b031fd7849c289b35caa45d03420
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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