Iodoethane → Ethyl 6-quinolyl ether

HRID 2257175Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH2:14](I)[CH3:15]>>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:15]

Participants

Reactant 3

HCID 6340Iodoethane

HCID 113746-Hydroxyquinoline

HCID 24758Sodium hydride

Product 1

HCID 89883Ethyl 6-quinolyl ether

Procedure

6-Hydroxyquinoline was treated with sodium hydride and ethyl iodide to give 6-ethoxyquinoline. This material was nitrated, reduced and coupled with 2-hexylthiodecanoic acid according to the procedure of Example 33 to give the title compound.

Sources & evidence

ORD record: ord-fab88e9b67684efa939c683bf1221a8f
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656634

Reaction notes

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