Lithium hydroxide, monohydrate → 6-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

HRID 1802184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802184
[F:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 67776717Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

Produkt 1

HCID 677761426-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acidAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (600 mg, 2.21 mmol) and lithium hydroxide monohydrate (186 mg, 4.42 mmol) in tetrahydrofurane (10 ml) and water (2.0 ml) is stirred for 3 hours at 25° C. The solvent is evaporated, the residue diluted with water (ca 10 ml) and acidified with 2N aqueous hydrochloric acid (2.2 ml), the precipitated red solid is collected by filtration, washed with water and dried affording 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (497 mg. 87.4%) as a pink solid. Mp.: >250° C. MS: m/z=329.2 (M−H+).

Aufarbeitung

  1. customThe solvent is evaporated
  2. additionthe residue diluted with water (ca 10 ml)
  3. filtrationthe precipitated red solid is collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d95b8057d3434cfe89fb35309b9c2907
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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