Sodium Hydroxide → 4-[(4-Amino-2-bromophenylthio)methyl]pyridine

Participants

Reaction Conditions

Reaction Steps

4-[(2-Bromo-4-nitrophenylthio)methyl]pyridine (D14) (0.800 g, 2.56 mmol) was dissolved in ethanol (40 ml) and heated to 60° C. with stifling. A solution of tin (II) chloride (1.696 g, 8.96 mmol) in conc. HCl (8 ml) was then added dropwise. The reaction mixture was heated under reflux for 2 h, then allowed to cool, diluted with water (40 ml) and basified to pH14 by the addition of 10% sodium hydroxide. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with dichloromethane (2×70 ml). The combined organic layers were then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a brown oil, which was dried in vacuo (0.670 g, 93%).

Provenance & Evidence