Dichloromethane → 5-Amino-6-chloro-2-methylisoindolin-1-one

Participants

Reaction Conditions

Reaction Steps

To 6-chloro-2-methyl-5-nitroisoindolin-1-one (340 mg, 1.5 mmol) in ethanol (9 mL) and water (0.9 mL) was added SnCl2.2H2O (1.35 g, 6 mmol) and the mixture was heated to 65° C. for 5 h. DCM (20 mL) and 2M NaOH(aq) (10 mL) were added and the mixture was passed through a hydrophobic frit. The solvent was removed in vacuo to give 5-amino-6-chloro-2-methylisoindolin-1-one (251 mg, 85%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=197 at 2.31 min. 1H NMR (400 MHz, d6-DMSO): δ 7.45 (s, 1H), 6.90 (s, 1H), 5.99 (br s, 2H), 4.32 (s, 2H), 3.01 (s, 3H).

Provenance & Evidence