Hydrochloric Acid → 2-[(Dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-[(dimethylamino)methyl]-2′-methylbiphenyl-4-carboxylate obtained in step 4 (687 mg; 2.42 mmol) in water (20 mL) at RT was treated with HCl (12 mL; 5 M; 60 mmol). The reaction mixture was refluxed at 105° C. for 4 hours, evaporated under vacuum, taken up in ACN and evaporated under vacuum to give the title compound as a light yellow powder (719 mg; 96%). 1H NMR (DMSO-d6) δ 13.23 (br s, 1H), 10.31 (br s, 1H), 8.47 (s, 1H), 8.03 (d, J=7.2 Hz, 1H), 7.38-7.31 (m, 4H), 7.20 (d, J=7.2 Hz, 1H), 4.32 (d, J=13.2 Hz, 1H), 3.87 (d, J=13.2 Hz, 1H), 2.61 (s, 3H), 2.50 (s, 3H), 1.98 (s, 3H). HPLC (Method A) Rt 2.52 min (Purity 100.0%).

Provenance & Evidence