Sodium Hydroxide → 4-methoxyquinaldine-N-oxide

HRID 1980476

Reaktionsgleichung

Reaktionsgleichung von HRID 1980476
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[CH:4]=1.[OH:14]C1C2C(=CC=CC=2)N=C(C)C=1.ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[N+:6]([O-:14])=[C:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 155606784-Methoxy-2-methylquinolineHCID 1784288112-Methylquinolin-4-ol

Produkt 1

HCID 204018894-methoxyquinaldine-N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

31 g of 4-methoxyquinaldine (prepared from 4-hydroxyquinaldine by the method of M. Maurin, A. Ch. 4 [11] (1935), 301 and 335) are taken up in 80 ml of chloroform at room temperature, and 42 g of 85% strength m-chloroperbenzoic acid are added a little at a time, with stirring. The mixture is heated at 40° C. for 2 hours and is then cooled to 20° C. and brought to pH 6-7 with about 9 g of NaOH in 50 ml of H2O. The organic phase is separated off, dried with Na2SO4, filtered and concentrated. 34 g of crude product remain, and are recrystallized from toluene with addition of a small amount of solid KOH. 12 g of pure 4-methoxyquinaldine-N-oxide are obtained. Melting point 131°-132° C.

Aufarbeitung

  1. temperatureis then cooled to 20° C.
  2. customThe organic phase is separated off
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customare recrystallized from toluene with addition of a small amount of solid KOH

Quellen und Nachweise

ORD-Eintrag
ord-053fda05c0284904ae7db291f2ab0146
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04510146

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