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

HRID 263965Notes

Reaction equation

HRID 263965 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([OH:15])[CH:9]=[CH:10][CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].C(OC1C=CC2C(=C(OCC(=O)C)C=CC=2)N=1)(=O)C>>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([O:15][CH2:17][C:18](=[O:19])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=[CH:10][CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6259Phenacyl bromideHCID 190360332-Acetoxy-8-(2-oxopropoxy)quinolineHCID 229959082-Acetoxy-8-hydroxyquinoline

Product 1

HCID 190360322-Acetoxy-8-(2-oxo-2-phenylethoxy)quinolineYield 74%

Procedure

2-Acetoxy-8-(2-oxo-2-phenylethoxy)quinoline (6a) was prepared from 2-acetoxy-8-hydroxyquinoline (5b) and 2-bromoacetophenone by the same procedure as 5c in 74% yield. mp: 141°-142° C.; 1H-NMR (CDCl3): δ1.92 (s, 3H, CH3), 5.66 (s, 2H, OCH2), 7.11 (d, 3-H), 7.25-8.04 (m, 8H, Ar--H), 8.05 (d, 4-H).

Sources & evidence

ORD record
ord-c7e7feab141245d4ab505a24cc81b34a
Source dataset
uspto-grants-1997_07
Patent number
US05646164

Reaction notes

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