Azobisisobutyronitrile → 6-(Bromomethyl)-2-methylquinoline

HRID 1173976

Reaktionsgleichung

Reaktionsgleichung von HRID 1173976
[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-621068ad687841ff8c58d580112f94c8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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