4-Amino-1-naphthalenecarbonitrile → 4-(Aminomethyl)naphthalen-1-amine

Temperature

70 °C

To a vial containing 4-aminonaphthalene-1-carbonitrile (0.59 mmol) was added BH3.THF (1M solution (1.2 mmol). The vial was capped and stirred at 70° C. for 19.5 hours. The reaction was cooled down to room temperature and quenched by drop wise addition of methanol (2 mL), stirred at room temperature for 30 minutes, filtered and stirred with Dowex 50WX2-200 resin (1 g) for 26.5 hours. The resin was filtered, washed with methanol (20 mL) and 10% aqueous ammonia (50 mL). The solvent was removed under vacuum. The material was used without any further purification in the next step.

1. customThe vial was capped
2. temperatureThe reaction was cooled down to room temperature
3. customquenched by drop wise addition of methanol (2 mL)
4. stirringstirred at room temperature for 30 minutes
5. filtrationfiltered
6. stirringstirred with Dowex 50WX2-200 resin (1 g) for 26.5 hours
7. filtrationThe resin was filtered
8. washwashed with methanol (20 mL) and 10% aqueous ammonia (50 mL)
9. customThe solvent was removed under vacuum
10. customThe material was used without any further purification in the next step

ORD record

ord-f46bacf9bd4f4633ae87241f3c9c8450

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741479B2