Selenium Dioxide → 4,6-Dimethyl-2-quinolinecarbaldehyde

HRID 655881Notes

Reaction equation

HRID 655881 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[Se](=O)=[O:15]>>[CH3:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=[C:2]([CH:1]=[O:15])[CH:11]=1

Participants

3

Reactant 2

HCID 24007Selenium DioxideHCID 752472,4,6-Trimethylquinoline

Product 1

HCID 114127864,6-Dimethyl-2-quinolinecarbaldehydeYield 61%

Procedure

The title compound was prepared from 2,4,6-trimethylquinoline (6a) and selenium dioxide using methods as described in the literature for similar compounds (Mathes et al., 1957) in 61% yield. 1H NMR (DMSO-d6, HMDSO), δ: 2.58 (3H, s); 2.72 (3H, s); 7.72 (1H, dd, J=1.8 Hz and J=8.6 Hz); 7.76 (1H, s); 7.92 (1H, unresolved d); 8.09 (1H, d, J=8.6 Hz), 10.05 (1H, s).

Sources & evidence

ORD record
ord-fb5b351e7767403e8ed80c603324f934
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

Loading…