Hydrochloric Acid → HCID 43299111, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (330 mg) and conc. hydrochloric acid (0.3 ml) were added to a solution of 1-(3-hydroxypropylthio)-4-nitrobenzene (Method 82; 1 g, 4.69 mmol) in ethanol (6 ml) and water (3 ml). The mixture was stirred and heated at 90° C. for 3 hours, further iron powder (300 mg) and conc. HCl (0.2 ml) were added and heating continued for a further 2 hours. The volatiles were removed by evaporation and water (20 ml) added to the residue. The mixture was acidified to pH 1 with 2M hydrochloric acid, filtered through diatomaceous earth, and the filtrate washed with EtOAc (2×25 ml). The aqueous layer was basified to pH11 with conc. aqueous sodium hydroxide solution and extracted with EtOAc (2×25 ml). The extracts were combined, washed with brine (15 ml), dried and evaporated under reduced pressure to give the title compound (900 mg, 100%). m/z 184.

Provenance & Evidence