Ammonia → 1-(2-Aminoethyl)-6-methoxyindan

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]#[N:14])=[CH:5][CH:4]=1.N>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][NH2:14])=[CH:5][CH:4]=1

Participants

Procedure

9.3 g (49 mmol) of crude 2-(6-methoxyindan-1-yl)acetonitrile are dissolved in 100 ml of methanol and, after the addition of 1 g of Raney nickel and 20 g of liquid ammonia, are hydrogenated at 70°-80° and 120 bar pressure. After 3 hours, the catalyst is filtered off from the methanolic solution and is subsequently washed with methanol. The methanolic solutions are combined and rendered acidic with hydrochloric acid. The acidic solution is concentrated to dryness by evaporation in vacuo, and the residue is dissolved in 100 ml of water, rendered alkaline with concentrated sodium hydroxide solution and extracted by shaking with diethyl ether. The ethereal phases are washed with saturated sodium chloride solution and dried over magnesium sulphate. After removing the solvent, crude 2-(6-methoxyindan-1-yl)ethylamine is obtained in the form of a yellow oil.