Thionyl Chloride → 4-(Chloromethyl)-2-methylquinoline

HRID 61434

Reaktionsgleichung

Reaktionsgleichung von HRID 61434
O[CH2:2][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.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:2][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

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 10149033(2-Methylquinolin-4-yl)methanol

Produkt 1

HCID 115357194-(Chloromethyl)-2-methylquinolineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-hydroxymethyl-2-methyl quinoline (7.0 g, 40 mmol) was dissolved in chloroform (150 mL) and cooled to 0° C., thionyl chloride (15.0 mL) was added slowly at this temperature and then the reaction mixture was allowed to warm up to room temperature and stirred overnight. The solvent was removed in-vacuo and the residue was titureted with ethyl acetate/ethyl ether to provide 9.0 g (100%) of 4-chloromethyl-2-methyl quinoline as an HCl salt. MS (ESI): 191.9 (M+H+).

Aufarbeitung

  1. temperatureto warm up to room temperature
  2. customThe solvent was removed in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-668a3648814747428598077790518b17
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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