Hydrochloric Acid → 4-(2-Methoxyphenoxy)-anilino-3-fluoro-6,7-dimethoxyquinoline

HRID 989059Notes

Reaction equation

Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][C:4]=1[F:17].[CH3:18][O:19][C:20]1[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=1[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>CCOCC.C1(O)CCCCC1>[CH3:18][O:19][C:20]1[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=1[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:5]2[C:4]([F:17])=[CH:3][C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of hydrogen chloride in ether (1 molar, 0.34 ml) was added to a mixture of 4-chloro-6,7-dimethoxy-3-fluoro-quinoline (80 mg) and 4-(2-methoxyphenoxy)-aniline (142 mg) in cyclohexanol (3 ml). The mixture was stirred and heated at 110° C. for 18 hours. The mixture was cooled to ambient temperature and then filtered. The crystals were washed with a small volume of diethyl ether and then dried to give 4-(2-methoxyphenoxy)-anilino-3-fluoro-6,7-dimethoxyquinoline (120 mg, 79%).

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationfiltered
washThe crystals were washed with a small volume of diethyl ether
customdried

Sources & evidence

ORD record: ord-a421ef169b7f49f48ac8ecbd26267ed7
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638945B1

Reaction notes

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