Hydrochloric Acid → HCID 67045281, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-nitro-2-(4-propyl-phenyl)-isoindole-1,3-dione (3.11 g, 10.03 mmol) obtained in Example 1 and tin (16.66 g, 140.39 mmol) in ethanol (125 ml) was added with concentrated hydrochloric acid (74 ml), and the mixture was stirred with heating at 75° C. for 8 hours. The reaction solution was cooled to room temperature, and then added to 2 N aqueous sodium hydroxide (220 ml), and the mixture was filtered through Cerite. The filtrate was added with chloroform for extraction. The chloroform layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=30:1) and recrystallization (ethanol) to obtain the objective compounds, 5-amino-2-(4-propyl-phenyl)-isoindol-1-one as a pale yellow powdery substance (1.13 g, yield: 42.3%) and 6-amino-2-(4-propyl-phenyl)-isoindol-1-one as a pale yellow powdery substance (0.27 g, yield: 10.2%).

Provenance & Evidence