2-Bromo-2-methyl-N-phenylpropanamide → 3,3-Dimethyl-1,3-dihydro-indol-2-one

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Reaction Steps

A neat mixture of AlCl3 (8.28 g) and the amide obtained in Step 1. above (5 g) is heated slowly to about 135°-140° C. and maintained at this temperature for about 10-15 min. Ice water is added slowly to the reaction mixture and the residue is extracted with ether. The organic extract is washed with 1N HCl, 10% aqueous sodium carbonate, dried, filtered and evaporated affording a solid. The solid is purified by flash chromatography (silica gel; 2% methanol/methylene chloride) affording the desired product as a white crystalline solid, M.P.=151°-152° C.

Provenance & Evidence