2,4-Dichlorobenzylamine → HCID 25029940, compound

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Reaction Steps

2-Ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid (0.061 g, 0.3 mmol, prepared as described below) was dissolved in anhydrous dimethylformamide (5 ml) and to this was added 1-hydroxybenzotriazole (0.045 g, 0.3 mmol), diisopropylethylamine (0.105 ml, 0.6 mmol), [(2,4-dichlorophenyl)methyl]amine (0.054 g, 0.3 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.114 g, 0.3 mmol). The mixture was stirred for 3 hrs and then left to stand overnight. The mixture was diluted with water (50 ml) and a little saturated aqueous sodium chloride solution and extracted with ethyl acetate (3×20 ml). The organic fractions were combined and washed with 10% aqueous sodium carbonate (50 ml) and then with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulphate and evaporated to give a gum. The gum was purified by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-2-ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxamide (0.056 g).

Provenance & Evidence