Sodium Hydroxide → 3-(Pyridin-3-yloxy)aniline

Participants

Reaction Steps

Compound 4 (1.613 g, 7.461 mmol, 1.000 eq) was dissolved in 1N HCl in MeOH (75 mL) and zinc (1.46 g, 22.3 mmol, 3.00 eq) was added. The reaction was stirred for 1 hour and additional zinc (975 mg, 14.9 mmol, 2 eq) was added to drive the reaction to completion as determined by TLC. The reaction was neutralized with 1N NaOH (75 mL), filtered and extracted (3×) with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 555 mg (85%) of the title compound as a brown oil: 1H NMR (400 MHz, DMSO-d6) δ 8.33-8.31 (m, 2H), 7.39-7.38 (m, 2H), 7.01 (t, J=8.0 Hz, 1H), 6.35 (dd, J=8.0, 1.6 Hz, 1H), 6.19 (t, J=2.2 Hz, 1H), 6.14 (dd, J=7.9, 2.0 Hz, 1H), 5.27 (s, 2H); ES-MS [M+1]+: 187.2.

Provenance & Evidence