2-Cyanomethyl-6-methoxy-1-tetralone → HCID 12832408, compound

Reaction equation

[C:1]([CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]1=O)#[N:2].[H][H]>C(O)C.[Ni]>[CH3:15][O:14][C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[CH:4]([CH2:3][CH2:1][N:2]=3)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

Procedure

The solution of 50 g of 2-cyanomethyl-6-methoxy-1-tetralone in 1000 ml of ethanol is hydrogenated in the presence of 15 g of Raney nickel at atmospheric pressure and room temperature until 2 mole equivalents of hydrogen are consumed. The mixture is filtered, the filtrate evaporated and the crude product dissolved in 500 ml of N hydrochloric acid. The solution is washed with diethyl ether, treated with charcoal, filtered and the filtrate is basified with 3 N aqueous sodium hydroxide. It is extracted with methylene chloride, the extract dried, evaporated, the residue crystallized from petroleum ether and recrystallized from hexane, to yield the 7-methoxy-3,3a,4,5-tetrahydro-2H-benz[g]indole melting at 102°-104°.