Hydrochloric Acid → HCID 57436585, compound

Participants

Reaction Steps

To a stirring solution of 2-(3-cyanophenyl)-4-nitroanisole from Example 111 (4.0 g, 16 mmol) in tetrahydrofuran (100 mL) was added borane-tetrahydrofuran complex dropwise (48 mL of a 1.0 M solution in tetrahydrofuran, 3 equiv, 48 mmol). The solution was heated to reflux for 3 hours. The solution was allowed to cool to room temperature and hydrochloride acid (24 mL of 4.0 M solution in dioxane, 96 mmol) was added slowly. Methanol (100 mL) was added slowly and the solution was evaporated to dryness. The residue was diluted with methanol (100 mL) and evaporated to dryness. The residue was dissolved in dichloromethane (100 mL). A clear solution was achieved, from which a precipitate began to form (<1 min). The solution was stirred at room temperature for 14 hours and the solid was collected on a Büchner funnel, washed with dichloromethane (10 mL), and dried under high vacuum to afford 2-(3-aminomethylphenyl)-4-nitroanisole hydrochloride (2.26 g, 55% yield).

Provenance & Evidence