Sodium Hydroxide → 2-(Methylamino)quinoline-6-carboxylic acid

HRID 711076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711076
[OH-].[Na+].[CH3:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=2)[N:6]=1>C(O)C>[CH3:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=2)[N:6]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57861311Ethyl 2-(methylamino)quinoline-6-carboxylate

Produkt 1

HCID 674914872-(Methylamino)quinoline-6-carboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Aqueous sodium hydroxide (4 mL, 8 mmol, 2 N) was added to a solution of ethyl 2-(methylamino)quinoline-6-carboxylate (850 mg, 3.7 mmol) in ethanol (10 mL). The reaction was heated to 50° C. overnight. Ethanol was removed in vacuo and the residue was acidified to pH=5 with 1 N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (710 mg, 96%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 8.26 (d, 1H), 7.96-7.93 (m, 2H), 7.50 (d, 1H), 7.43 (d, 1H), 6.81 (d, 1H), 2.91 (d, 3H).

Aufarbeitung

  1. customEthanol was removed in vacuo
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a45b5add0ffe48a6825b5381b594738f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181252B2

Notizen zur Reaktion

Wird geladen…