N-(2-ethyl-6-nitrophenyl)acetamide → 2-Ethyl-6-nitroaniline

Participants

Reaction Steps

A solution of N-(2-ethyl-6-nitrophenyl)actamide (Example 139e) (0.62 g, 2.98 mmol) in EtOH (21 mL) and concentrated HCl (13 mL) was refluxed for 24 h. EtOH was evaporated, the residue was diluted with water (10 mL) and the pH was adjusted to pH˜8 with NaOH (2.0M aqueous solution). The neutralized solution was extracted with EtOAc (3×50 mL), the combined extract was washed with water and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified on HPLC to give 0.32 g (64%) of 2-ethyl-6-nitroaniline as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 7.82-7.87 (m, 1H), 7.27-7.32 (m, 1H), 7.16 (broad s, 2H), 6.55-6.62 (m, 1H), 2.55 (q, J=7.2 Hz, 2H), 1.13 (t, J=7.2 Hz, 3H).

Provenance & Evidence