Ammonia → 1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanone (90.0 mg, 0.45 mmol), titanium(IV) isopropoxide (255 mL, 0.90 mmol) and 2 M solution of ammonia in ethanol (1.10 mL, 2.26 mmol) were stirred at room temperature for 6 h. The reaction was cooled to 0° C. and sodium borohydride was added portionwise during 10 min. (25.5 mg, 0.67 mmol); the resultant mixture was stirred at rt for an additional 3 h. The reaction was quenched by pouring it into ammonium hydroxide (2 M, 10 mL), the precipitate that formed was filtered off and washed with ethyl acetate (5 mL×3). The organic layer was separated and the remaining aqueous layer was extracted with ethyl acetate (5 mL×2). The combined organic extracts were washed with 1 M HCl (5 mL). The acidic aqueous extracts were washed with ethyl acetate (15 mL), then treated with aqueous sodium hydroxide (2 M) to pH 10-12, and extracted with ethyl acetate (15 mL×3). The combined organic extracts were washed with brine (5 mL), dried (Na2SO4), and concentrated in vacuo to afford the desired product (50 mg, 56% yield). 1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanone:

Provenance & Evidence