Ammonium Chloride → HCID 21106349, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-iodo-5-nitro-1H-indole III (20 g, 69.4 mmol) in methanol (650 mL) at 25° C. was treated with a solution of ammonium chloride (26.1 g, 485.8 mmol) in water (550 mL) and iron powder (13.6 g, 242.9 mmol). The mixture was heated to 100° C. under a nitrogen atmosphere for 5 h. The resulting mixture was filtered through a pad of celite and the celite pad washed with hot methanol. The filtrate was concentrated in vacuo and the residue was partitioned between methylene chloride and water and separated. The pH of the aqueous layer was adjusted to pH=10 with ammonium hydroxide and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to a volume of 250 mL. This solution was treated with a 4.0M aqueous hydrochloric acid solution in dioxane and stirred at 25° C. for 2 h. The precipitate was collected by filtration and washed with methylene chloride and petroleum ether to afford 7-iodo-1H-indol-5-ylamine hydrochloride IV (24.7 g, quant.) as a gray solid: 1H NMR (DMSO-d6, 300 MHz) δ 11.34 (broad s, 1H), 9.93 (broad s, 2H), 7.56 (d, J=1.46 Hz, 1H), 7.48 (t, J=2.74 Hz, 1H), 7.44 (d, J=1.83 Hz, 1H), 6.68 (dd, J1=1.83 Hz, J2=2.93 Hz, 1H).

Provenance & Evidence