4-Amino-m-cresol → HCID 19923004, Verbindung

HRID 1534493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534493
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][O:18]C(=O)C1C=CC=CC=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].O[C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[C:30]([CH3:35])[CH:29]=1>O1CCOCC1>[ClH:16].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:32][C:31]1[CH:33]=[CH:34][CH:28]=[CH:29][C:30]=1[CH3:35])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][OH:18])(=[O:5])[CH:2]([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 178194-Amino-m-cresolHCID 10384366HCID 10384366, Verbindung

Produkt 1

HCID 19923004HCID 19923004, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-isobutyryl-4-chloro-8-(benzoyloxymethyl)quinoline (3.68 g, 10 mmol) and 4-hydroxy-2-methylaniline (1.35 g, 11 mmol) in dioxan (50 ml) was heated at reflux for 2 hours, then the dioxan evaporated and the residue taken up in 1% methanolic sodium hydroxide (100 ml) and stirred 1.5 hours at room temperature. The methanol was evaporated, the residue taken up in water, adjusted to pH 7, and the solid filtered off. This was converted to the salt with ethanolic hydrogen chloride, then recrystallized from aqueous ethanol to give 3-isobutyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline hydrochloride (1.15 g, 30%), m.p. 225°-255° (dec).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customthe dioxan evaporated
  3. customThe methanol was evaporated
  4. filtrationthe solid filtered off
  5. customrecrystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-176bd702acdc4e34a895452d5a92e0ed
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089504

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