Lithium hydroxide, monohydrate → 7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid

HRID 51914

Reaction equation

HRID 51914 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=1)[CH:10]=2)=[O:5])C.O.[OH-].[Li+]>O1CCCC1CO.O>[F:33][C:30]([F:31])([F:32])[C:27]1[CH:28]=[CH:29][C:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([NH:16][C:11]2[CH:10]=[C:9]3[C:14]([CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[CH:13][CH:12]=2)=[O:34])=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 698913457-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 227368887-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Procedure

7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester (180 mg, 0.387 mmol) was dissolved in 5 ml of a 3:1:1 mixture of tetrahydrofuran-methanol-water, and lithium hydroxide monohydrate (50 mg, 1.16 mmol) was added. After 18 h at reflux, the volatiles were removed under vacuum and water was added to the mixture, which was acidified with 1N HCl, extracted with ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered and concentrated under vacuum to provide the title compound.

Workup

  1. additionwas added
  2. temperatureAfter 18 h at reflux
  3. customthe volatiles were removed under vacuum and water
  4. additionwas added to the mixture, which
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f6885f161344179923e12c020df2da1
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Linked notes

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