Sodium Acetate → 1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Participants

Reaction Steps

To a solution of 5.2 g of N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide obtained in stage d) below in 140 mL of dimethylformamide are added 2.12 g of N,N,N-triethylethanaminium chloride, 1.4 g of sodium formate and 3.4 g of sodium acetate. After stirring for 30 minutes under argon at room temperature, 410 mg of palladium diacetate are added and the mixture is heated at 80° C. for 5 hours. After cooling to room temperature, the reaction mixture is diluted with one litre of water, and the solid formed is filtered off and washed with four times 40 mL of water. The solid is then dissolved in 200 mL of ethyl acetate, dried over magnesium sulphate in the presence of 0.5 g of vegetable charcoal, filtered and concentrated under reduced pressure to give 3 g of 1-acetyl-3,3-dimethyl-6-nitroindoline in the form of a beige-yellow solid, the characteristics of which are as follows:

Provenance & Evidence