Hydrochloric Acid → 2-Aminobenzaldehyde

Participants

Reaction Steps

Iron powder (39 g; 700 mmol) and concentrated hydrochloric acid (0.583 mL; 7 mmol) were added to a solution of 2-nitrobenzaldehyde (10.58 g; 70 mmol) in a mixture ethanol (210 mL)-water (52 mL). The well-stirred reaction mixture was heated to reflux for 5 h. After cooling, the suspension was filtered on a plug of celite, washed with ethanol and the filtrate was concentrated under reduced pressure until the organics were removed. The remaining aqueous layer was extracted with ethyl acetate, the organics were combined, dried over sodium sulfate, concentrated under reduced pressure to furnish 8.2 g (96%) of 2-aminobenzaldehyde as a yellow oil, which crystallized slowly. ESI/APCI(+): 122 (M+H). NMR 1H (CDCl3) (ppm): δ 9.87 (s, 1H, CHO); 7.48 (dd, 1H, Harom.); 7.31 (td, 1H, Harom.); 6.75 (td, 1H, Harom.); 6.51 (dd, 1H, Harom.); 6.11 (bs, 2H, NH2).

Provenance & Evidence