Lithium Hydroxide → 6-(3-Cyanophenyl)nicotinic acid

HRID 602110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602110
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Li+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67268247Methyl 6-(3-cyanophenyl)nicotinate

Produkt 1

HCID 178779506-(3-Cyanophenyl)nicotinic acidAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of methyl 6-(3-cyanophenyl)nicotinate (300 mg, 1.26 mmol) and 2 M lithium hydroxide solution (1.89 mL) in tetrahydrofuran (30 mL) was heated at 40° C. overnight. The tetrahydrofuran was evaporated off, water (5 mL) was added and the reaction mixture was acidified to pH 6 with 2N aqueous HCl. The precipitated solid was filtered off and dried under vacuum to give 6-(3-cyanophenyl)nicotinic acid (208 mg). 1H NMR (400 MHz, DMSO-d6) ppm 7.74 (t, J=7.8 Hz, 1H), 7.96 (m, 1H), 8.23 (m, 1H), 8.36 (m, 1H), 8.49 (m, 1H), 8.55 (m, 1H), 9.15 (m, 1H), 13.5 (broad s, 1H) LCMS 225 (M+1) ELSD 1.33 minutes.

Aufarbeitung

  1. customThe tetrahydrofuran was evaporated off
  2. additionwater (5 mL) was added
  3. filtrationThe precipitated solid was filtered off
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d4ef6a80bd6e45d6a214323ff72212b6
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902373B2

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