HCID 21914164, compound → HCID 57436580, compound

Participants

Reaction Steps

2-(3-cyanophenyl)-4-nitroanisole (8.0 g) from Example 111, part a, was dissolved in THF (200 mL) and purged with nitrogen. A 11.0M solution of borane in THF (135 mL) was then added, and the reaction was heated at reflux for 4 hours. When the reaction was complete, the mixture was cooled to room temperature and 4.0N HCl in dioxane (25 mL) was added dropwise over 30 minutes. Methanol (200 mL) was slowly added to the acidified solution, and the solvent was removed in vacuo. The resulting gum was redissolved in methanol (150 mL) and concentrated in vacuo to give a solid. The product was dissolved in dichloromethane (150 mL) and cooled to −20° C. to give 2-(3-aminomethylphenyl)-4-nitroanisole which was collected on a filter and dried in vacuo.

Provenance & Evidence