Acetic Anhydride → 5-Iodo-1-methyl-3,4-dihydroisoquinoline

Participants

Reaction Steps

N-(2-iodophenethyl)acetamide. A solution of 2-(2-iodophenyl)ethanamine (13.5 g, 54.6 mmol) and Ac2O (10.3 mL, 109 mmol) in 1,4-dioxane (200 mL) was heated to 100° C. for 45 min. The reaction was then allowed to cool to RT and concentrated in vacuo. The resulting residue was taken up in DCM and washed with a saturated aq. solution of NaHCO3—gas formation! The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a yellow oil (16.2 g) which was used as it is in the next step. UPLC-MS: MS 290.3 (M+H+); UPLC rt 0.96 min.

Provenance & Evidence