Sulfuric Acid → 3-Acetyl-2,4-dihydroxyquinoline

HRID 982859

Reaktionsgleichung

Reaktionsgleichung von HRID 982859
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14].C(OCC)C.C[O-].[Na+].S(=O)(=O)(O)O>CO.CCCCCC.CCOC(C)=O.C(Cl)Cl.CC(C)=O>[C:13]([C:12]1[C:11](=[O:16])[NH:10][C:5]2[C:4]([C:3]=1[OH:17])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:15])[CH3:14]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 459324Methyl 2-(3-oxobutanoylamino)benzoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 546825123-Acetyl-2,4-dihydroxyquinolineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 19841213hexane EtOAc CH2Cl2 acetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

2-(3-Oxo-butanoylamino)-benzoic acid methyl ester (383 mg, 1.63 mmol) was combined with diethyl ether (10 mL) and methanol (5 mL) and the mixture was stirred rapidly while a solution of sodium methoxide (25% solution, 1.63 mmol, 0.45 mL) in methanol (3 mL) was added over 10 minutes. The reaction then was heated at 40° C. overnight. Progress of the reaction was monitored by TLC (silica gel, hexane:EtOAc:CH2Cl2:acetone (3:3:3:1)) and analytical HPLC and upon its completion the mixture was acidified with 1 N sulfuric acid to form a solid. The solid was collected by filtration and then crystallized from hot acetic acid/acetonitrile/water to provide 3-acetyl-4-hydroxy-1H-quinolin-2-one (250 mg, 76%) as small colorless prisms, mp 258-262° C. (dec) (lit., 259° C.). LCMS MH+ 204.2.

Aufarbeitung

  1. additionwas added over 10 minutes
  2. customThe reaction
  3. customto form a solid
  4. filtrationThe solid was collected by filtration
  5. customcrystallized from hot acetic acid/acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-00197e51198a4654b57c1e32b14c6f7f
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861419B2

Verknüpfte Notizen

Wird geladen…