6-Methylquinoline → 6-Quinolinecarbaldehyde

HRID 22916

Reaction equation

HRID 22916 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.[Se](=O)=[O:13].CCCCC.CCOC(C)=O>CO>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 70596-MethylquinolineHCID 8003PentaneHCID 8857Ethyl AcetateHCID 24007Selenium Dioxide

Product 1

HCID 7656536-QuinolinecarbaldehydeYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

6-Methyl-quinoline (Aldrich Chemical Co.) (1 g, 7.0 mmol) and selenium dioxide (2.32 g, 21.0 mmol) were combined in the absence of solvent and heated at 100° C. under a nitrogen atmosphere for 16 h. The reaction mixture was allowed to cool to room temperature, taken up in MeOH and presorbed onto silica gel. Chromatography using a 3:1 mixture of pentane: EtOAc provided the title product (236 mg, 21%); 1HNMR (400 MHz, CDCl3) δ: 7.46-7.52 (m, 2H), 7.98 (d, 1H), 8.33-8.37 (m, 2H), 9.03 (d, 1H), 10.18 (s, 1H); m/z (ES+) 315 (2MH+).

Workup

  1. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-f0e5f8f1f26f46a1b8c680a466a37ac9
Source dataset
uspto-grants-2005_02
Patent number
US06849649B2

Linked notes

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