Benzyl Bromide → 8-(Benzyloxy)quinoline-2-carbaldehyde

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Se](=O)=[O:22]>>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:22])[CH:8]=[CH:7]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 132242-Methyl-8-hydroxyquinoline

HCID 24007Selenium Dioxide

Product 1

HCID 15347698-(Benzyloxy)quinoline-2-carbaldehydeYield 35%

Procedure

The title compound was prepared from 8-hydroxy-2-methylquinoline (6d), benzyl bromide, and selenium dioxide using methods as described in the literature for similar compounds (Buchi et al., 1956) in 35% yield.

Sources & evidence

ORD record: ord-6a88e0122d0a4e8e83c17bb26252aae9
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652036B2

Reaction notes

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