Aniline → [6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

HRID 25750

Reaktionsgleichung

Reaktionsgleichung von HRID 25750
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH:11]=2)[NH:6][C:5]([CH3:22])([CH3:21])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CS(C)=O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([CH3:22])([CH3:21])[CH:4]=[C:3]2[CH2:2][NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Produkt 1

HCID 10406857[6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 60 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline in 1 mL of DMSO was treated with 46 mg of potassium carbonate and 17 μL of aniline at room temperature. The resulting mixture was stirred at room temperature overnight. Then the mixture was quenched with water and the product was extracted into EtOAc. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 9 mg of the title compound as a foam.

Aufarbeitung

  1. customThen the mixture was quenched with water
  2. extractionthe product was extracted into EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-89326becbe274adc9dc4ba83d715c9c3
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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