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

反応式

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

参加物

実験手順

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.