Ammonium Chloride → 2-Methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinamine

Participants

Reaction Steps

To a solution of 2-methyl-3-nitro-6-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine (200 mg, 0.673 mmol) in ethanol (6 mL) and water (2 mL) was added ammonium chloride (17.99 mg, 0.336 mmol) and iron powder (113 mg, 2.018 mmol). The reaction mixture was heated at reflux under nitrogen for 1 hour. The reaction mixture was filtered through a pad of celite and the pad washed with ethyl acetate. The combined filtrate and washings were separated between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with water and brine, then dried over magnesium sulphate and evaporated in vacuo to give the title product (153 mg) as a pale brown gum. LCMS (2 min, formic) Rt 0.35 min, m/z (ES+) 268 (M+H).

Provenance & Evidence