Thionyl Chloride → 5-(1-Chloroethyl)quinoline

HRID 1174680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174680
[N:1]1[C:10]2[C:5](=[C:6]([CH:11](O)[CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)[CH3:12]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 687709021-(Quinolin-5-yl)ethanol

Produkt 1

HCID 597495555-(1-Chloroethyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The alcohol, 1-quinolin-5-yl-ethanol (5.0 g, 28.9 mmol) in chloroform was treated with a dropwise addition of thionyl chloride (5.26 mL, 72.1 mmol) at rt. After 1 h the mixture was cooled to 0° C. and carefully quenched with a sat. solution of NaHCO3 followed by 2M NaOH until the pH was >8. The aqueous layer was extracted with chloroform and the organic fractions were combined, dried over MgSO4, filtered, and freed of solvent. The residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate:hexane. The product, 5-(1-chloro-ethyl)-quinoline (Intermediate E1) was obtained as a clear oil, 4.22 g (76%).

Aufarbeitung

  1. customcarefully quenched with a sat. solution of NaHCO3
  2. extractionThe aqueous layer was extracted with chloroform
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-70e57606b3484548b3398863bf487520
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838545B2

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