1,2-Dichlorobenzene → 4-(5-Chloro-7-methyl-quinolin-6-yloxy)-6,7-dimethoxy-quinoline

HRID 228881Notes

Reaction equation

Br[C:2]1[C:11]([OH:12])=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.[Cl:29]C1C=CC=CC=1Cl>CN(C)C1C=CN=CC=1>[Cl:29][C:2]1[C:11]([O:12][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 140 °C

Procedure

5-Bromo-6-hydroxy-7-methyl-quinoline (110 mg), 4-chloro-6,7-dimethoxyquinoline (330 mg), and 4-dimethylaminopyridine (240 mg) were suspended in o-dichlorobenzene (10 ml), and the mixture was stirred at 140° C. for 6 hr. The reaction solution was cooled to room temperature, and the solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (19 mg, yield 10%).

Workup

temperatureThe reaction solution was cooled to room temperature
customthe solvent was removed
distillationby distillation under the reduced pressure
customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-c6d4e4992f244669b0443c109f795087
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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