Sodium Hydroxide → 6-Carboxy-4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline

HRID 393667Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([C:17]([O:19]C)=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:25])[CH:3]=1.[OH-].[Na+]>CO.O>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:21][CH3:22])[N:10]=[CH:9][CH:8]=[C:7]2[NH:6][C:5]1[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][C:4]=1[F:25])([OH:19])=[O:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-methoxycarbonylquinoline (1.79 g, 4.9 mmol), (prepared as described in Example 55), and sodium hydroxide (0.6 g, 15 mmol) in methanol (75 ml) and water (5 ml) was heated at 70° C. for 4 hours. The mixture was allowed to cool and the volatiles were removed by evaporation. The solid residue was suspended in water and acetic acid was added to adjust the aqueous suspension to pH5. The mixture was stirred for 15 minutes and the solid product was collected by filtration, washed with water and then acetone and finally ether, and dried to give 6-carboxy-4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline (1.55 g, 90%).

Workup

temperatureto cool
customthe volatiles were removed by evaporation
additionacetic acid was added
filtrationthe solid product was collected by filtration
washwashed with water
dry with materialacetone and finally ether, and dried

Sources & evidence

ORD record: ord-fb7c19e83af14bb8900343397ae3b7dc
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Reaction notes

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