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

HRID 2042103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042103
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18504229Ethanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c627adf8e7b5469cb03f8c3c8cc837fc
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586565B2

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