Sodium Hydroxide → 4-Amino-6-methoxyquinoline-3-carboxylic acid

HRID 2047708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047708
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH2:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[Na+]>CCO>[NH2:16][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 16644472Ethyl 4-amino-6-methoxyquinoline-3-carboxylate

Produkt 1

HCID 166444904-Amino-6-methoxyquinoline-3-carboxylic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of ethyl-4-amino-6-methoxyquinoline-3-carboxylate (Example 1a, 1.23 g, 5.0 mmol) in EtOH (20.0 mL) was added aqueous NaOH (2.0 N, 5.0 mL) at room temperature. The reaction mixture was then refluxed for 3 hr. The solution was then filtered and washed with water. The filtrate was cooled to 0° C. and neutralized carefully with 1 N HCl to pH 7. Most of the EtOH was removed under reduced pressure, and the precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as an off-white solid (1.01 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 3.89 (s, 3H), 7.40 (dd, J=2.8, 9.4 Hz, 1H), 7.73 (d, J=9.4 Hz, 1H), 7.77 (d, J=2.8 Hz, 1H), 8.77 (s, 1H). MS 219 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 3 hr
  2. filtrationThe solution was then filtered
  3. washwashed with water
  4. customMost of the EtOH was removed under reduced pressure
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with cold water
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c5b81637e54241f5a79caee9c45ecd9a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592592B2

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