4-(2-methoxyphenoxy)aniline → 4-(2-Methoxyphenoxy)-anilino-3-bromo-6,7-dimethoxyquinoline

HRID 393569Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1Cl)=[CH:9][C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=2.[CH3:17][O:18][C:19]1[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=1[O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>C1(O)CCCCC1>[CH3:17][O:18][C:19]1[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=1[O:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:3]2[C:2]([Br:1])=[CH:11][C:10]3[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=3)[N:4]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-bromo-4-chloro-6,7-dimethoxyquinoline (302 mg) and 4-(2-methoxyphenoxy)-aniline (236 mg) in cyclohexanol (5 ml) was stirred and heated at 130° C. for 24 hours. The mixture was cooled to ambient temperature and then filtered. The crystals were washed first with methanol and then with diethyl ether and then dried to give 4-(2-methoxyphenoxy)-anilino-3-bromo-6,7-dimethoxyquinoline (Compound 2) (180 mg, 37%).

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationfiltered
washThe crystals were washed first with methanol
dry with materialwith diethyl ether and then dried

Sources & evidence

ORD record: ord-59f6b19c59f64d719f70bf1cc9adb12c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809106B1

Reaction notes

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