Methanol → HCID 178487707, Verbindung

HRID 2044013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044013
[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14]C)=[O:13])[CH:8]=[C:7]2[OH:16].CO.C1COCC1.[Li+].[OH-]>O>[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[C:7]2[OH:16]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178498513HCID 178498513, Verbindung

Produkt 1

HCID 178487707HCID 178487707, VerbindungAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 8-chloro-4-hydroxy-7-methoxyquinoline-2-carboxylate (36.5 g, 0.145 mol) in a mixture of 1:1 of MeOH: THF (160 mL total) was added a solution of LiOH (30.5 g, 0.725 mol) in H2O (80 mL). The mixture was stirred at room temperature for an hour when LCMS analysis showed complete conversion to the carboxylic acid. The reaction was worked up by removal of the volatiles and adjusting the pH of the solution to 6 using aqueous 6N HCl. The resulted gummy residue was filtered and dried on the lypholizer for 2 days to provide 34.4 g (99.6%) of the product as a white solid. EI MS (m/z) 253.9 [M+H].

Aufarbeitung

  1. customThe reaction was worked up by removal of the volatiles
  2. filtrationThe resulted gummy residue was filtered
  3. customdried on the lypholizer for 2 days

Quellen und Nachweise

ORD-Eintrag
ord-a2caa3c26a6741d9ab2971c4d599e29e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586744B2

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