Water → (s)-1-(3-Nitrophenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-(3-nitrophenyl)-1-azidoethane (1.55 mmol) in benzene (8 mL) was added water (1.0 mL) and triphenylphosphine (3.18 mmol). The resulting mixture was heated to 80° C. for 19 h. This mixture was cooled, diluted with diethyl ether (50 mL) and washed with 50 mL of 2N aqueous HCl. The aqueous phase was made basic by adding 50 mL of 5N aqueous NaOH then extracted with diethyl ether (3×50 mL). These ether extracts were combined, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified on silica gel in 3%(2M NH3 in MeOH)/CH2Cl2 to yield 78.4 mg of pure title compound and 159 mg of the title compound that is approximately 80% pure by NMR. 1H NMR (500 MHz, CDCl3): δ 8.23 (m, 1H); 8.06 (m, 1H); 7.70 (d, J=8.1 Hz, 1H); 7.48 (t, J=8.1 Hz, 1H); 4.25 (q, J=6.9 Hz, 1H); 1.40 (d, J=6.9 Hz, 3H).

Provenance & Evidence