Hydrochloric Acid → 2-Methyl-6-(trifluoromethyl)nicotinic acid

HRID 2180899

Reaktionsgleichung

Reaktionsgleichung von HRID 2180899
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6][C:5]=1[CH3:14].O.[OH-].[Li+].C(OCC)(=O)C.Cl>CO.O>[CH3:14][C:5]1[N:6]=[C:7]([C:10]([F:13])([F:11])[F:12])[CH:8]=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 2779428Methyl 2-methyl-6-(trifluoromethyl)nicotinate

Produkt 1

HCID 27756832-Methyl-6-(trifluoromethyl)nicotinic acidAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

6.68 g (0.0305 mol) of 2-methyl-6-trifluoromethyl-nicotinic acid methyl ester (prepared in the manner described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/water (3:1 mixture) and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added in portions at 22° C. After 4 hours at 22° C., the reaction mixture is added to ethyl acetate and 2N hydrochloric acid; the organic phase is washed three times with water, dried with sodium sulfate and concentrated by evaporation, and the residue is triturated with a small amount of hexane. After filtering, 5.69 g (90% of theory) of the expected 2-methyl-6-trifluoromethyl-nicotinic acid having a melting point of 147-149° C. are obtained.

Aufarbeitung

  1. washthe organic phase is washed three times with water
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe residue is triturated with a small amount of hexane
  5. filtrationAfter filtering

Quellen und Nachweise

ORD-Eintrag
ord-6786c08f58184e3793d5a6323c3caed0
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06890885B2

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