Ethyl Acetate → 2-isopropyl-5-methoxyaniline

Participants

Reaction Steps

To a solution of 2-(2-amino-4-methoxyphenyl)propan-2-ol (210 mg; 1.2 mmol; 1 eq) in a mixture of EtOH (10 mL), EtOAc (3 mL) and 5 N (1 mL) under nitrogen atmosphere is added palladium on charcoal (130 mg; 10%) and the reaction mixture is hydrogenated for 1 week at room temperature at 1 atmosphere. The catalyst is filtered through celite and the organic solvents are removed under vacuum. The residue is taken up in EtOAc. The organic phase is washed with a saturated aqueous solution of Na2CO3 and dried over MgSO4. The solvent is evaporated under reduced pressure to afford 160 mg (84%) of the title compound as a red oil. The compound is used in the next step without further purification. 1H NMR (DMSO-d6) δ 6.89 (d, J=9.0 Hz, 1H), 6.18 (d, J=3.0 Hz, 1H), 6.05 (dd, J=9.0, 3.0 Hz, 1H), 5.45-5.39 (m, 2H), 3.85 (s, 3H), 3.30-3.11 (m, 1H), 1.97 (s, 6H). HPLC (max plot) 70%; Rt 1.88 min.

Provenance & Evidence