Ethyl Acetate → 5-Aminoisoquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-nitro-isoquinoline (150 g, 0.861 mol) in EtOH/H2O=4:1 (5 L) was added NH4Cl (92.2 g, 1.723 mol) and Fe (193 g, 3.445 mol) at room temperature. Then the mixture was heated to 80° C. and stirred for 10 hours. TLC (petroleum ether:ethyl acetate=1:1) showed complete conversion. The mixture was cooled to room temperature and filtered through a pad of celite. The filter cake was washed with EtOH (2 L×2) and the filtrate concentrated under vacuum. The residue was extracted with EtOAc (500 mL×10) and the combined layers dried over Na2SO4, filtered and then concentrated under vacuum to afford 5-amino-isoquinoline (67 g, 54%) as a yellow solid.

Provenance & Evidence