Methoxyacetyl chloride → N-(3-Ethynylphenyl)-2-methoxyacetamide

Participants

Reaction Steps

To a cooled solution of 3-ethynylphenylamine (7.02 g, 60 mmol) in methylene chloride is added a solution of methoxyacetyl chloride (7.8 g, 72 mmol) in methylene chloride (10 mL) dropwise over a period of 30 min at 0° C. After addition, the reaction mixture is allowed to warm-up to room temperature and stirred overnight. The solvent is evaporated and the residue is partitioned between water and ethyl acetate. The organic phase is washed with saturated NaHCO3, H2O, dried (MgSO4) and concentrated to afford the title compound as a colorless oil 10.2 g (90%). 1HNMR (CDCl3): δ (ppm) 3.04 (s, 1H,), 3.48 (s, 3H), 3.98 (s, 2H), 7.24 (m, 2H), 7.61 (d, 1H), 7.66 (s, 1H), 8.21 (s, b, 1H).

Provenance & Evidence