Hydrochloric Acid → HCID 57436585, compound

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).

1. temperatureThe solution was heated
2. temperatureto reflux for 3 hours
3. customthe solution was evaporated to dryness
4. additionThe residue was diluted with methanol (100 mL)
5. customevaporated to dryness
6. dissolutionThe residue was dissolved in dichloromethane (100 mL)
7. customto form (<1 min)
8. customthe solid was collected on a Büchner funnel
9. washwashed with dichloromethane (10 mL)
10. customdried under high vacuum

ORD record

ord-baf0b8aa8c0148e2976707276f2b4a66

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582765B2