Hydrochloric Acid → Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

HRID 502624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502624
[C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:3])[CH3:2].[CH3:25][Mg]Cl.[NH4+].[Cl-].Cl>C1COCC1>[OH:3][C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:25])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 86098625Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl esterHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 86611056Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl ester (3.58 g, 10.5 mmol) in 40 mL of THF was cooled to around −20 to −25° C. Methyl magnesium chloride (5.25 mL of 3M solution in THF) was added dropwise over a period of 10 minutes. The reaction mixture was allowed to stir 18 hours at ambient temperature, and then was poured into saturated aqueous NH4Cl and acidified with 1N HCl to pH 5. The resulting mixture was extracted with ethyl acetate and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated to dryness under reduced pressure to give 3.75 g of toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester as an oil that solidified on standing.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b93517d03ef4298bef0557c4050d7aa
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776872B2

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