Dimethylformamide → HCID 353402, compound

Participants

Reaction Steps

3.0 g (21.9 mmol) of the 3-hydroxybenzamide prepared in Example 1 and 5.7 g (41.2 mmol) of anhydrous potassium carbonate were added to a round bottom flask followed by 40 ml anhydrous DMF added by syringe. To this mixture was added 11.85 g (70.9 mmol, 7.8 cc) of 2-acetoyl ethyl bromide, also using a syringe to maintain anhydrous conditions. The suspension was stirred for 48 hr and the mixture filtered. The solid was washed with 6×5 ml DMF and the filtrate evaporated in vacuo to a solid. The resulting solid was recrystallized from 90% aqueous alcohol and the solid from the filtration was washed with cold 90% alcohol and ether. The desired product, 3-(2-acetoylethoxy)benzamide was obtained in 65% yield (3.2 g), mp 121°-122° C. Identity of the product was confirmed by TLC and by elemental analysis. Calculated for C11H13NO4 ; C: 59.18; H: 5.87; N: 6.28; Found: C: 59.03; H: 5.83; N: 6.58.

Provenance & Evidence