Lithium Hydroxide → 2-Methoxy-7-quinolinecarboxylic acid

HRID 880950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880950
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([C:13]([O:15]CC)=[O:14])=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Li+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([C:13]([OH:15])=[O:14])=[CH:8][CH:9]=2)[N:4]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67491407Ethyl 2-methoxyquinoline-7-carboxylate

Produkt 1

HCID 674915922-Methoxy-7-quinolinecarboxylic acidAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-methoxyquinoline-7-carboxylate (125 mg, 0.54 mmol) in tetrahydrofuran (1.5 mL) was added 2 N aqueous lithium hydroxide (0.81 mL, 1.6 mmol). The reaction was stirred at room temperature for 65 hours. The tetrahydrofuran was removed in vacuo and the residue was acidified to pH=4 with 1 N aqueous hydrochloric acid. The mixture was diluted with water and the resulting precipitate was collected by filtration and dried under vacuum to give the title compound (106 mg, 96%) as a white solid. +ESI (M+H) 204.2; 1H NMR (400 MHz, CDCl3, δ): 8.64 (d, J=1.37 Hz, 1H), 8.01-8.04 (m, 1H), 8.01 (s, 1H), 7.79 (d, J=8.58 Hz, 1H), 7.01 (d, J=8.78 Hz, 1H), 4.09 (s, 3H).

Aufarbeitung

  1. customThe tetrahydrofuran was removed in vacuo
  2. additionThe mixture was diluted with water
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-da4f35e07a8e4729a41af1a56693aff1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993586B2

Notizen zur Reaktion

Wird geladen…