Lithium Hydroxide → 2-Carboxy-6-chloro-7-methyl-4-oxoquinoline

HRID 1827860

Reaktionsgleichung

Reaktionsgleichung von HRID 1827860
C[O:2][C:3]([C:5]1[CH2:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][C:9]([CH3:17])=[C:10]([Cl:16])[CH:11]=2)[N:6]=1)=[O:4].[OH-].[Li+]>CO.O>[C:3]([C:5]1[CH2:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][C:9]([CH3:17])=[C:10]([Cl:16])[CH:11]=2)[N:6]=1)([OH:4])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 684363462-Methoxycarbonyl-6-chloro-7-methyl-4-oxoquinoline

Produkt 1

HCID 684353962-Carboxy-6-chloro-7-methyl-4-oxoquinolineAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Methoxycarbonyl-6-chloro-7-methyl-4-oxoquinoline (7.00 g, 28.00 mmol) was suspended in 300 mL of MeOH and 100 mL of water. Lithium hydroxide (3.40 g, 90 mmol) was added and the reaction was stirred at room temp for 2 hours. The methanol was evaporated in vacuo and the product was crystallized by addition of 2N hydrochloric acid. The solid was filtered, washed with water and dried to afford 5.9 g (88%) of 2-carboxy-6-chloro-7-methyl-4-oxoquinoline: H NMR (DMSO-d6) 2.40 (s, 3), 6.60 (s, 1), 7.84 (s, 1), 7.98 (s, 1) ppm.

Aufarbeitung

  1. customThe methanol was evaporated in vacuo
  2. customthe product was crystallized by addition of 2N hydrochloric acid
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1c10e45740f04fab90378d6c39366700
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056923B2

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