Water → 6-bromo-2,2-dimethyl-1H-quinoline

HRID 1009140

Reaktionsgleichung

Reaktionsgleichung von HRID 1009140
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:13])([C:11]#[CH:12])[CH3:10])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O>[Cu]Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:9]([CH3:13])([CH3:10])[CH:11]=[CH:12]2

Komponenten

6

Edukt 3

HCID 962WaterHCID 1140TolueneHCID 200822714-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

Produkt 1

HCID 157119676-bromo-2,2-dimethyl-1H-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine (3.30 g, 14 mmol) in toluene (14 ml, 14 mmol) was added copper(I) chloride (0.300 g, 3.0 mmol) in one portion. The reaction vessel was sealed and the resulting mixture was heated to 90 deg C. After stirring overnight, the mixture was transferred to a separatory funnel containing water and EtOAc. The aqueous layer was washed 1× with EtOAc and 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated. The crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH)) to provide the product. MS m/z: 238.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturethe resulting mixture was heated to 90 deg C
  3. customthe mixture was transferred to a separatory funnel
  4. washThe aqueous layer was washed 1× with EtOAc and 3× with DCM
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))
  9. customto provide the product

Quellen und Nachweise

ORD-Eintrag
ord-5d8ba509bda54ef5bc355e7f6d6687cb
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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