Hydrazine hydrate (1:1) → 4-chloro-5-methoxy-1H-indole

Participants

Reaction Steps

A solution of 2-nitro-5-methoxy-6-chloro-β-pyrrolidinostyrene (5.28 g, 18.7 mmol) in benzene (100 ml) was stirred under nitrogen at 20° C. Raney nickel (0.50 ml) was added, followed by hydrazine hydrate (1.6 ml). After 30 minutes, more hydrazine hydrate was added (1.6 ml), and the mixture was stirred for a further 11/2 hours. After filtration through celite, the filtrate was evaporated to dryness to leave a dark yellow crystalline residue, which was purified by chromatography (SiO2 ; CHCl3), then recrystallised from benzene/hexane to give 4-chloro-5-methoxyindole (2.85 g) m.p. 112°-3° C.

Provenance & Evidence