Triphenylphosphine → 2-Nitrophenethylamine

To a solution of 1-(2-Bromoethyl)-2-nitrobenzene (6.96 g, 30.5 mmol) in CH3CN was added a solution of NaN3 (6 g, 91.6 mmol) in water (20 ml) and the reaction mixture was refluxed for 20 hours. The solution was cooled and extracted with DCM (3×). The organics were combined, washed with brine, dried (MgSO4) and evaporated to dryness. The residue was taken up in toluene (160 ml) and to this was added PPh3 (8 g, 30.5 mmol) and the reaction mixture was stirred at RT for 16 hours. The solvent was evaporated to dryness and the residue was treated with acetic acid (30 ml) and 48% HBr in acetic acid (30 ml) at 100° C. for 1 h. The reaction mixture was cooled, concentrated and extracted with DCM. The aqueous was brought to pH ˜10 with NaOH (aq.) and extracted with EtOAc (3×). The organics were combined, washed with brine, dried (MgSO4) and evaporated to dryness (4.2 g).

1. temperaturethe reaction mixture was refluxed for 20 hours
2. temperatureThe solution was cooled
3. extractionextracted with DCM (3×)
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. customevaporated to dryness
7. customThe solvent was evaporated to dryness
8. additionthe residue was treated with acetic acid (30 ml) and 48% HBr in acetic acid (30 ml) at 100° C. for 1 h
9. temperatureThe reaction mixture was cooled
10. concentrationconcentrated
11. extractionextracted with DCM
12. extractionextracted with EtOAc (3×)
13. washwashed with brine
14. dry with materialdried (MgSO4)
15. customevaporated to dryness (4.2 g)

ORD record

ord-5e5cb3df13bc46f4a9ccbaa7759c344b

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834000B2