Ammonium Chloride → HCID 86595125, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-iodo-2-methyl-5-nitro-2,3-dihydro-1H-indole XIV (4.75 g, 0.0156 mol) in methanol (150 mL) at 25° C. was treated with a solution of ammonium chloride (5.22 g, 0.0976 mol) in water (150 mL) and iron powder (3 g, 0.0534 mol). The mixture was heated to 100° C. under a nitrogen atmosphere for 6 h. The reaction mixture was filtered hot through a pad of celite and washed with hot methanol. The filtrate was concentrated in vacuo and the residue partitioned between methylene chloride and water. The layers were separated and the pH of the aqueous layer was adjusted to pH=10 with ammonium hydroxide. The aqueous layer was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to a volume of 50 mL. The resulting solution was treated with a 4.0M aqueous hydrochloric acid solution in dioxane and then stirred at 25° C. for 1 h. The precipitate was collected by filtration and washed with methylene chloride and petroleum ether to afford 7-iodo-2-methyl-1H-indol-5-ylamine hydrochloride XV (4.37 g, 81%) as a gray solid: LRMS for freebase C9H11IN2 (M+H)+ at m/z=275.

Provenance & Evidence