Lithium hydroxide, monohydrate → 5-Chloro-2-(quinolin-6-yl)benzoic acid

HRID 1711683Notes

Reaction equation

HRID 1711683 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].O[Li].O>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67253873Ethyl 5-chloro-2-(quinolin-6-yl)benzoate

Product 1

HCID 672545235-Chloro-2-(quinolin-6-yl)benzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirring solution of ethyl 5-chloro-2-(quinolin-6-yl)benzoate (0.244 g, 0.78 mmol) in 1:1:1 THF/EtOH/H2O (21 ml) at RT was added LiOH—H2O (0.164 g, 3.91 mmol). The resulting reaction mixture was stirred at RT overnight. Solvent was removed under reduced pressure and the residue was diluted with H2O (10 mL). The aqueous solution was acidified to pH˜4 with 3M HCl and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4) and concentrated to afford 5-chloro-2-(quinolin-6-yl)benzoic acid (0.201 g, 91% yield) as a white solid. MS (ESI) m/z: 284.0 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. customSolvent was removed under reduced pressure
  3. additionthe residue was diluted with H2O (10 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f37de7481e4f4a5db40db182df442091
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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