Hydrochloric Acid → 4-Chloro-2-cyclopropylaniline

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(4-chloro-2-cyclopropylphenyl)acetamide (689 mg, 3.29 mmol) in 2M HCl (aq) (25 ml, 823 mmol) was stirred at 100° C. for 3 hrs and then 90° C. for 16 hrs. The resulting mixture was cooled to RT, diluted with EtOAc and water and the layers separated. The organic layer was extracted with 0.1 M HCl (aq) and the organic portion was discarded. To the combined aqueous portions was added 2M NaOH (aq) until basic and resulting mixture was extracted with EtOAc (2×). The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a dark yellow oil.

Provenance & Evidence