Ammonium Hydroxide → 3-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

Participants

Reaction Steps

Add sodium borohydride (0.58 g, 15.26 mmol) to a solution of 1-[2-(2-chloro-4-nitro-phenoxy)-ethyl]-pyrrolidine (0.83 g, 3.07 mmol) and NiCl2.6H2O (1.45 g, 6.12 mmol) in MeOH (20 mL). Stir at room temperature for 2 h and add 10% NH4OH solution. Extract with CH2Cl2 and then EtOAc, combine the organics, dry, and concentrate. Purify by flash chromatography using 0-10% 2N NH3/MeOH in CH2Cl2, to give the title compound (0.5 g, 69%). MS (ES+) 241.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 6.78 (d, 1H, J=8.4 Hz), 6.72 (d, 1H, J=3.1 Hz), 6.51 (dd, 1H, J=8.4, 3.1 Hz), 4.07 (t, 2H, J=6.2 Hz), 3.47 (s, 2H), 2.90 (t, 2H, J=6.2 Hz), 2.64 (m, 4H), 1.79 (m, 4H).

Provenance & Evidence