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

HRID 6681

Reaktionsgleichung

Reaktionsgleichung von HRID 6681
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-11b76eafc4824bf4a143a7e2a8c5476d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084142B2

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