Triphenylphosphine → 2-(3-Nitrophenyl)ethan-1-amine

A mixture of 3-nitrophenethyl azide (0.9 g, 4.69 mmol), triphenyl phosphine (1.22 g, 4.66 mmol) and CH2Cl2 (80 mL) was stirred at room temperature for 3 days. Solvent was removed and the residue was taken up in EtOH (20 mL). The solution was heated to 70° C., added 2M NaOH aqueous solution (10 mL) and stirred at room temperature for 2 hrs. A 10% HCl aqueous solution (20 mL) was then added and refluxed for 2 hrs. After the mixture cool to room temperature, it was washed with benzene, basified with 5N NaOH to pH-12, extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the product (0.63 g) as a yellow oil.

1. customSolvent was removed
2. temperatureThe solution was heated to 70° C.
3. additionadded 2M NaOH aqueous solution (10 mL)
4. stirringstirred at room temperature for 2 hrs
5. additionA 10% HCl aqueous solution (20 mL) was then added
6. temperaturerefluxed for 2 hrs
7. temperatureAfter the mixture cool to room temperature
8. washit was washed with benzene
9. extractionextracted with ethyl acetate
10. dry with materialThe organic layer was dried over Na2SO4
11. concentrationconcentrated

ORD record

ord-e4762eb872244a0d8ddfd5713acab851

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140318