4-Methoxy-3-nitrobenzonitrile → 3-Amino-4-methoxybenzonitrile

Participants

Reaction Steps

A mixture of 8.8 g of Compound 18A and 46.8 g of stannous chloride dihydrate in 250 mL of 95% ethanol was refluxed for 1 hour. The solvent was evaporated off in vacuo and the residue was taken up with 200 mL of water. The mixture was acidified with 37% HCl, then alkalinised with 35% sodium hydroxide and extracted with 3×200 mL of diethyl ether. The combined organic layers were washed with 50 mL of water, dried over sodium sulphate and evaporated to dryness in vacuo to afford 6.90 g (94.2%) of Compound 18B as an ivory solid.

Provenance & Evidence