Selenium Dioxide → 5-Bromo-6-methoxy-2-quinolinecarbaldehyde

HRID 655882Notes

Reaction equation

HRID 655882 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.[Se](=O)=[O:16]>>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:14]=[O:16])=[N:7]2

Participants

3

Reactant 2

HCID 24007Selenium DioxideHCID 114252565-Bromo-6-methoxy-2-methylquinoline

Product 1

HCID 575169515-Bromo-6-methoxy-2-quinolinecarbaldehydeYield 75%

Procedure

The title compound was prepared from 5-bromo-6-methoxy-2-methylquinoline (6b) and selenium dioxide using methods as described in the literature for similar compounds (Mathes et al., 1957) in 75% yield. 1H NMR (DMSO-d6, HMDSO), δ: 4.07 (3H, s); 7.92 (1H, d, J=9.0 Hz); 8.03 (1H, d, J=9.2 Hz); 8.29 (1H, d, J=9.2 Hz); 8.58 (1H, d, J=9.0 Hz), 10.09 (3H, s).

Sources & evidence

ORD record
ord-f05654ec13ed4363be9af5af93ef0de8
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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