Nitrogen → HCID 22504099, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the 1-naphthylacetylchloride (21.90 g, 107.0 mmol) in CH2Cl2 (100 mL) was added dimethylhydroxyl amine hydrochloride (13.57 g, 139.1 mmol) and the solution cooled to 0° C. Et3N (43.20 mL, 31.32 mmol) was added to the solution dropwise under an atmosphere of N2. The mixture was then allowed to warm to room temperature where it was stirred for 12 hours and then filtered to remove a white solid. The filtrate was concentrated under vacuum and the residue was diluted with EtOAc (100 mL) and then was washed with 1 N HCl (50 mL), saturated NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried (MgSO4) and then stripped of solvent under vacuum. The crude product was subjected to silica gel chromatography (EtOAc/Hexanes, 1:9) to give N-methoxy-N-methyl-2-naphthalen-1-yl-acetamide 16.90 g (69%) as a white solid: 1H-NMR (400 MHz, CDCl3) δ 8.06 (dd, 1 H), 7.87 (dd, 2H), 7.77 (dd, 1 H), 7.56-7.39 (m, 4 H), 4.22 (s, 2H), 3.60 (s, 3H), 3.22 (s, 2H).

Provenance & Evidence