Dichloromethane → 4-Amino-5-chloro-2-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To 5-chloro-2-methyl-4-nitrobenzonitrile (192 mg, 1 mmol) in ethanol (6 mL) and water (0.6 mL) was added SnCl2.2H2O (903 mg, 4 mmol) and the mixture was heated to 65° C. for 5 h. DCM (10 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 4-amino-5-chloro-2-methylbenzonitrile (131 mg, 81%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=163 at 3.37 min. 1H NMR (400 MHz, CDCl3): δ 6.89 (s, 1H), 6.52 (s, 1H), 4.21 (br s, 2H), 3.84 (s, 3H), 2.38 (s, 3H).

Provenance & Evidence