Ammonium Chloride → 2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)aniline

反応式

[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH2:4][CH2:3]1.[NH4+].[Cl-]>CO.[Zn]>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:4][CH2:3]1

参加物

実験手順

The crude 1c (0.66 g) was stirred in MeOH (20 mL) at rt. Solid NH4Cl (0.62 g) was added, followed by addition of Zn dust (3.0 g) portionwise. The resulting mixture was stirred at rt for 2 h. It was filtered through Celite®, rinsed with CH2Cl2, and concentrated to dryness. The residue was purified by flash chromatography (hexanes/EtOAc) to give pure amine 1d (0.43 g, 73% for two steps). LC-MS ESI 253 (M+H).