Dichloromethane → 4-Chloro-6-iodo-2-methoxy-3-(4-methylbenzyl)quinoline

HRID 926481Notes

Reaction equation

[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[C:13]([Cl:23])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([I:24])[CH:11]=2)[N:6]=1.ClCCl>C1(C)C=CC=CC=1>[Cl:23][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([I:24])[CH:11]=2)[N:6]=[C:5]([O:2][CH3:1])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Sodium methoxide (3.2 g, 60 mmol) was added to a solution of 2,4-dichloro-6-iodo-3-(4-methylbenzyl)quinoline (4.3 g, 10 mmol, Intermediate 22: step b) in toluene (50 mL) with stirring. The mixture was heated to 105° C. After 18 hours, the flask was allowed to cool to 23° C. Dichloromethane (100 mL) was added and then the mixture was filtered through Celite®. The filter cake was washed with dichloromethane. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel eluting with hexanes initially, grading to 20% ethyl acetate-hexanes to provide the title compound as a white solid.

Workup

temperatureto cool to 23° C
filtrationthe mixture was filtered through Celite®
washThe filter cake was washed with dichloromethane
concentrationThe filtrate was concentrated
customthe residue was purified by flash column chromatography on silica gel eluting with hexanes initially

Sources & evidence

ORD record: ord-455ce0cc417a49e9b050ffe0e5a741c3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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