Phenacyl bromide → 2-Methyl-8-(2-oxo-2-phenylethoxy)quinoline

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([O:22]CC(=O)C)[CH:16]=[CH:17][CH:18]=2)[N:13]=1>>[CH3:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([O:22][CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

Reactant 2

HCID 6259Phenacyl bromide

HCID 107274142-Methyl-8-(2-oxopropoxy)quinoline

Product 1

HCID 107076662-Methyl-8-(2-oxo-2-phenylethoxy)quinolineYield 72%

Procedure

2-Methyl-8-(2-oxo-2-phenylethoxy)quinoline (11a) was prepared from 2-bromoacetophenone by the same procedure as 10a in 72% yield. mp: 70°-71° C.; 1H-NMR (CDCl3): δ2.77 (s, 3H, 2-CH3), 5.63 (s, 2H, OCH2), 6.94-8.10 (m, 8H, Ar--H), 7.29 (d, 1H, 3-H), 7.99 (d, 1H, 4-H).

Sources & evidence

ORD record: ord-30c6e40533fd425799b94b5a78bfb9c5
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646164

Reaction notes

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