Lithium hydroxide, monohydrate → 5-Fluoro-3-methylpicolinic acid

HRID 1186207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186207
C[O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>CO.O>[F:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58563046Methyl 5-fluoro-3-methylpyridine-2-carboxylate

Produkt 1

HCID 582246285-Fluoro-3-methylpicolinic acidAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) in MeOH (6 ml) was added at 22° C. a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HCl. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z=153.7 [M−H]−.

Aufarbeitung

  1. customthe MeOH was evaporated at reduced pressure
  2. extractionThe aqueous layer was extracted with AcOEt
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residue was crystallized from AcOEt/n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-0fb1492b483b44eb80ec393f1987a487
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673894B2

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