Hydrochloric Acid → 3-(5-Methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoic acid

HRID 1845287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845287
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH:17]=2)[C:11]([O:13]C)=[O:12])=[N:6][CH:7]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH:17]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58188068Methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate

Produkt 1

HCID 581882003-(5-Methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate (240 mg, 0.74 mmol) in tetrahydrofuran (6 mL) was added 2.5 M of aqueous lithium hydroxide solution (1.6 mL, 4.1 mmol). The reaction mixture was stirred at 60° C. overnight. The aqueous solution was acidified with 15% HCl (aq.) to pH=5-6, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to get the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): 8.77 (s, 1H), 8.70 (s, 1H), 8.08 (s, 1H), 8.04 (s, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.64 (dd, J=8.0, 2.0 Hz, 1H), 7.25 (d, J=4.8 Hz, 1H), 6.85 (d, J=4.0 Hz, 1H), 2.41 (s, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic layers were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-db6f29517d5742bc8bf4704b51feddc2
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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