Azobisisobutyronitrile → 6-(Bromomethyl)-2-methylquinoline

HRID 348723

Reaktionsgleichung

Reaktionsgleichung von HRID 348723
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 134142,6-DimethylquinolineHCID 67184N-bromobutanimide

Produkt 1

HCID 27954806-(Bromomethyl)-2-methylquinolineAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

In carbon tetrachloride (26 ml), 2,6-dimethylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.0398 g), N-bromosuccinimide (1.2353 g), and azobisisobutyronitrile (98.5 mg) were dissolved and then the whole was subjected to thermal reflux for 2 hours under an argon atmosphere. After the reaction, a precipitate was removed through filtration and then washed with water, followed by drying with magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (427.3 mg) as a white solid.

Aufarbeitung

  1. temperaturethermal reflux for 2 hours under an argon atmosphere
  2. customAfter the reaction
  3. customa precipitate was removed through filtration
  4. washwashed with water
  5. dry with materialby drying with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d6b0d115572c49eeb8bce110d6f0dab3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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