Hydrochloric Acid → Phthalimidine

Participants

Reaction Steps

To a suspension of phthalimide (14.7 g, 100.0 mmol) in AcOH (150 mL) was added Sn0 (29.7 g, 250.0 mmol) and concentrated HCl (70 mL). The mixture was heated to reflux for two hours. The hot mixture was filtered and concentrated. The residue was taken up in CH2Cl2 and washed four times with 1M HCl, until no more precipitate was observed when saturated NaHCO3 was added to the organic phase. The organic layer was washed once with saturated NaHCO3, dried over MgSO4, filtered and concentrated to provide the title compound as a pale yellow solid (7.00 g, 53%). 1H NMR (300 MHz, CDCl3): δ 8.08 (d of d, 1H), 7.52 (m, 3H), 4.50 (s, 2H).

Provenance & Evidence