4-Toluenesulfonyl chloride → 2-(Chloromethyl)-6-fluoroquinoline

HRID 1091091

Reaktionsgleichung

Reaktionsgleichung von HRID 1091091
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-])=[C:7]([CH3:13])[CH:6]=[CH:5]2.C1(C)C=CC(S([Cl:23])(=O)=O)=CC=1>ClC(Cl)C>[Cl:23][CH2:13][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 15675913HCID 15675913, Verbindung

Produkt 1

HCID 112410072-(Chloromethyl)-6-fluoroquinolineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Fluoro-2-methylquinoline N-oxide (2.70 g, 15.25 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (2.9 g, 15.21 mmol) in dichloroethane (100 mL). The reaction mixture was heated to 100° C. overnight under N2, cooled and concentrated, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4 and evaporated under reduced pressure to afford a solid. The crude solid was purified by flash chromatography (15:1 hexane/ethyl acetate) to afford 1.59 g (63%) of pure product as an off white solid.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. custompartitioned between 10% K2CO3 /ethyl acetate
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto afford a solid
  7. customThe crude solid was purified by flash chromatography (15:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-594b55aaa1164d53880d6e1351d45fbb
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05084463

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