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

HRID 1597146Notes

Reaction equation

HRID 1597146 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][CH2:8][N:9]=[N+]=[N-])([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][CH2:8][NH2:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 224575343-Nitrophenethyl azide

Product 1

HCID 129500662-(3-Nitrophenyl)ethan-1-amineYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

  1. customSolvent is removed
  2. temperatureThe solution is 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) is then added
  6. temperaturerefluxed for 2 hrs
  7. temperatureAfter the mixture cool to room temperature
  8. washit is washed with benzene
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer is dried over Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ec5f274b9a754f74a9ae132f48149ec3
Source dataset
uspto-grants-2001_09
Patent number
US06294529B1

Reaction notes

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