4-Chloro-6,7-dimethoxyquinoline → 4-(2-Iodo-4,5-dimethyl-phenoxy)-6,7-dimethoxyquinoline

HRID 228687

Reaction equation

[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[O:10][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Iodo-4,5-dimethylphenol (447 mg), 4-chloro-6,7-dimethoxyquinoline (466 mg), and 4-dimethylaminopyridine (539 mg) were suspended in o-dichlorobenzene (20 ml), and the mixture was stirred at 130° C. for 4 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-chloroform to give the title compound (452 mg, yield 50%).

Workup

temperatureThe reaction solution was cooled to room temperature
customthe solvent was then removed by distillation under the reduced pressure
additionWater was then added to the residue
extractionthe mixture was extracted with chloroform
washThe chloroform layer was washed with water
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-375447432ad448ada733883bacae3148
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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