Lithium Hydroxide → 5-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid

HRID 2409775Notes

Reaction equation

HRID 2409775 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:16]2[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=2[Cl:27])=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)=[O:5])C.[Li+].[OH-].C1COCC1>O>[Cl:27][C:17]1[C:18]([O:25][CH3:26])=[CH:19][C:20]([O:23][CH3:24])=[C:21]([F:22])[C:16]=1[C:9]1[CH:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59292845HCID 59292845, compound

Product 1

HCID 866411485-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(2-chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 176.2) (235 mg, 0.60 mmol), a 2 N aqueous solution of LiOH (3 mL) and THF (3 mL) was stirred for 20 h at rt, diluted with H2O and extracted with Et2O. The aqueous layer was acidified to pH 4 by addition of a 2 N aqueous solution of HCl. The resulting white precipitate was collected by vacuum filtration providing 210 mg of the title compound: ESI-MS: 362.1 [M+H]+; tR=4.24 min (System 1).

Workup

  1. extractionextracted with Et2O
  2. additionThe aqueous layer was acidified to pH 4 by addition of a 2 N aqueous solution of HCl
  3. filtrationThe resulting white precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-5b8ff1cc286d4594bc4b202849c3383a
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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