Diethyl Ether → 8-Methoxy-1,2,3,4-tetrahydro-9-acridinamine

反応式

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:11])[C:8]=1[C:9]#[N:10].CCO[CH2:15][CH3:16]>[N+](C1C=CC=CC=1)([O-])=O.C1(=O)CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:8]=1[C:9]([NH2:10])=[C:15]1[C:16]([CH2:4][CH2:3][CH2:8][CH2:7]1)=[N:11]2

参加物

反応条件

温度: 125 °C

実験手順

6-Methoxyanthranilonitrile (14.0 g) was dissolved in nitrobenzene (150 ml) and cyclohexanone (18.45 g), and freshly fused zinc chloride (25.6 g) was added. The reaction mixture was warmed at 125° C. for 1.5 hr, cooled to room temperature, and poured into ether (1 l). The solid was collected, washed with ether, and distributed between 2-butanone and ammonium hydroxide. The organic phase was washed with brine, dried, filtered, and evaporated. The residue was recrystallized two times from ethyl acetate to give 13.7 g (63.8%), mp 187°-188° C.