Hydrazine hydrate (1:1) → 5-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

5-Chloro-3-(2,2-dimethyl-2-nitroethyl)-1H-indole (13.5 g, 53.1 mmol), prepared as in Example 2, Step (b), was dissolved in ethanol (≈100 mL). An aqueous suspension of RANEY NICKEL® catalyst (5.0 mL) was added to the solution and the mixture was heated to 80° C. Hydrazine hydrate (10 mL, 321.1 mmol) in ethanol (≈30 mL) was added dropwise to the mixture which was then stirred for an additional 30 minutes. The mixture was filtered through celite and the filter cake was washed with methanol. The filtrate was concentrated by rotary evaporation to ≈75 mL. Crystallization upon addition of water gave [2-(5-chloro-1H-indol-3-yl)-1,1-dimethylethyl]amine (9.17 g, 40.9 mmol), m.p. 156°-158° C.

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