7-HYDROXY-2-METHYLISOINDOLIN-1-ONE

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,4,5-trichloropyrimidine (0.20 g) and 7-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one are dissolved in DCM (10 mL), cooled to 0° C. and combined with caesium carbonate (0.75 g). The cooling bath is removed and the mixture is stirred for 16 h. For working up the mixture is combined with 10% NaCl solution (100 mL) and extracted three times with 75 mL ethyl acetate. The combined organic phases are dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. The cooling bath is removed extracted three times with 75 mL ethyl acetate The combined organic phases are dried on magnesium sulphate filtered off from the desiccant and the solvent

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2.49 g (91.5 mmol) of 7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one were dissolved at 0° C. in 6 ml of concentrated sulfuric acid. The reaction medium was cooled to −20° C. and 1.8 ml of a 4/5 mixture of concentrated sulfuric acid/nitric acid at 70% were added. After 10 minutes, the reaction medium was hydrolyzed with water. Sodium chloride was added and the medium was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a C18 column twice (40 g prepacked column, water/acetonitrile gradient). 350 mg of product were obtained in the form of a yellow solid. Yield=11%. were added the medium was extracted twice with ethyl acetate dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a C18 column twice (40 g prepacked column, water/acetonitrile gradient)

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 100 ml of a 1 M solution of boron tribromide in dichloromethane at −78° C. were added dropwise to a solution of 3.7 g of 7-methoxy-2-methyl-2,3-dihydroisoindol-1-one in 50 ml of dichloromethane. The reaction medium was stirred at −78° C. for 1 hour and then left to return to 0° C. for 1 hour. The reaction medium was cooled to −78° C. and then slowly hydrolyzed by adding, dropwise, 20 ml of methanol (temperature below −60° C.). The reaction medium was washed with 30 ml of a 1 M sodium dihydrogen phosphate solution and the aqueous phase was extracted with ethyl acetate (2×50 ml). The organic phases were combined, dried over magnesium sulfate and evaporated. The residue was triturated with diethyl ether. 2.6 g of 7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one were obtained. left to return to 0° C. for 1 hour The reaction medium was cooled to −78° C. slowly hydrolyzed by adding The reaction medium was washed with 30 ml of a 1 M sodium dihydrogen phosphate solution the aqueous phase was extracted with ethyl acetate (2×50 ml) dried over magnesium sulfate evaporated The residue was triturated with diethyl ether