Sodium Bicarbonate → Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester

HRID 502625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502625
O[C:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3].C([O-])(O)=O.[Na+]>C(O)=O.[Zn]>[CH:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3]

Komponenten

5

Edukt 2

HCID 516892Sodium Bicarbonate2×HCID 86611056Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

Produkt 1

HCID 86611057Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl esterAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester (3.75 g, 10.5 mmol) was stirred in 50 mL of formic acid for 10 minutes, and zinc dust (3.43 g, 5.25 mmol) was added. The reaction mixture was stirred for four hours and then was added cautiously to a mixture of 100 mL aqueous saturated NaHCO3 and 100 g of ice. The resulting aqueous mixture was neutralized to pH7 by addition of aqueous saturated NaHCO3, and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography using silica eluting with 10% ethyl acetate in hexanes to afford 1.35 g of toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c07a2b81b6724bf7a03e9e9481bef52e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776872B2

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