Sodium Hydroxide → 2-(8-Trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoic acid

HRID 224592Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17].[OH-].[Na+]>CO>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1.45 g of the product of Example 11, 4 ml of 2 N sodium hydroxide solution and 21 ml of methanol was refluxed and the methanol was evaporated. 25 ml of water were added to the mixture and the solution was filtered through asbestos. The solution was heated to 60° C. and was acidified with concentrated hydrochloric acid. The resulting suspension was cooled and filtered and the recovered precipitate was washed with water and dried to obtain 1.26 g of 2-(8-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoic acid melting at 265°±3° C.

Workup

temperaturewas refluxed
customthe methanol was evaporated
addition25 ml of water were added to the mixture
filtrationthe solution was filtered through asbestos
temperatureThe resulting suspension was cooled
filtrationfiltered
washthe recovered precipitate was washed with water
customdried

Sources & evidence

ORD record: ord-7606fe2189d140119282c23c395500aa
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04233305

Reaction notes

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