Sodium Carbonate → 5-amino-2-(cyclopropylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione

Participants

Reaction Conditions

Reaction Steps

N-Cyclopropylmethyl-4-nitrophthalimide (6.0 g, 24 mmol) in methanol (200 mL) was added dropwise over 30 min to a solution of sodium dithionite (27.0 g, 156 mmol) and sodium carbonate (13.0 g, 125 mmol) in water (200 mL) while the temperature was maintained at 70° C. The mixture was stirred at 70° C. for an additional 50 min before it was allowed to cool to room temperature. The reaction volume was then reduced to one-third by rotary evaporation. Water (400 mL) was added, and the suspension extracted with ethyl acetate (2×450 mL). The combined organic solutions were dried with anhydrous MgSO4. Solvent was then removed by rotary evaporation to afford 2.52 g (49%) of pure N-cyclopropylmethyl-4-aminophthalimide as a powder.

Provenance & Evidence