Thionyl Chloride → 3-(Chloromethyl)quinoline hydrochloride

HRID 477705

Reaktionsgleichung

Reaktionsgleichung von HRID 477705
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11]O)[CH:2]=1.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[ClH:15].[Cl:15][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Komponenten

4

Edukt 2

HCID 24386Thionyl Chloride2×HCID 12662983(Quinolin-3-yl)methanol

Produkt 1

HCID 145481263-(Chloromethyl)quinoline hydrochlorideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of 2.53 g (15.9 mmol) of 3-quinolinemethanol in 25 mL of toluene was added dropwise at room temperature 5 mL of thionyl chloride. The reaction mixture was stirred at that temperature for 4 hours, then dried in vacuo to give which was suspended in 20 mL of toluene and treated with 4 mL of thionyl chloride at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give 2.05 g (60%) of a solid. The product, having the structural formula ##STR83## was not further purified. NMR (DMSO-d6) δ 9.36 (1H, d), 9.1 (1H, bs), 8.6-7.8 (4H, m), 5.2 (2H, s).

Aufarbeitung

  1. customdried in vacuo
  2. customto give which
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e19efe1536434cecb0b08ea01c637447
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888427

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