Hydrochloric Acid → 5-Amino-2,3-dihydro-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

Iron powder (158 mg, 2.83 mmol), water (61 μL), and HCl (37%, 5 μL, 0.566 mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-1-one (50.4 mg, 0.283 mmol) in EtOH (754 μL). The above mixture was heated at 95° C. for 2 h. After that time, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid was filtered off. The filtrate was concentrated in vacuo to obtain a light-yellow solid that was purified by preparative TLC eluting with 10% MeOH/CH2Cl2 to give a light-yellow solid of 5-amino-2,3-dihydroisoindol-1-one. 1H NMR (CD3OD, 400 MHz): δ=7.48 (s, 1H), 8.08 (s, 2H), 9.91 (s, 1H), 10.66 (d, 1H, J=8.8 Hz). MS (ES+): m/z 149.21 (100) [MH+]. HPLC: tR=1.20 min (ZQ2000, polar—5 min).

Provenance & Evidence