Hydroxyamine hydrochloride → (5-Chloro-1H-indol-3-yl)methanamine

Participants

Reaction Steps

A solution of 5-chloro-1H-indole-3-carbaldehyde (0.690 g; 3.76 mmol), hydroxylamine hydrochloride (0.366 g; 5.27 mmol) and sodium acetate (0.463 g; 5.65 mmol) in ethanol (10 mL) was stirred at reflux temperature for 3.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and brine and extracted with ethyl acetate. The solvent was evaporated and the residue (crude oxime) was dissolved in glacial acetic acid (30 mL). Zinc dust (1.48 g; 22.59 mmol) was added to the solution, and the mixture was stirred at room temperature for 14 hours. The resulting suspension was filtered on a Celite pad and the cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was partitioned between an aqueous solution of sodium carbonate and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 0.680 (88%) of (5-chloro-1H-indol-3-yl)methanamine as a brown solid.

Provenance & Evidence