Hydrazine hydrate (1:1) → 4-Chloro-5-n-propyloxyindole

Participants

Reaction Steps

Reaction of 2-chloro-3-n-propyloxy-6-nitrotoluene (8.50 g, 37.0 mmol) with dimethylformamide diethyl acetal (6.43 g, 43.7 mmol) and pyrrolidine (3.11 g, 43.7 mmol) in DMF and subsequent workup, as described in 1 (b), followed by treatment with hydrazine hydrate (2×2.7 ml) and Raney nickel (3.9 ml) in THF (70 ml) and methanol (70 ml), gave 4- chloro-5-n-propyloxyindole as an oil (1.37 g).

Provenance & Evidence