Lithium Hydroxide → 2-Methoxy-7-quinolinecarboxylic acid

HRID 537149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537149
[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-dcfe978371cf4706a452ef610ca86b56
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859773B2

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