Acetic Acid → 3-[(Ethyl-methyl-amino)-methyl]-5-methyl-benzoic acid

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Reaction Steps

To a solution of 3-formyl-5-methyl-benzoic acid (2.83 g, 17.2 mmol) in DCM (100 mL) and NMP (15 mL), AcOH (3.17 g, 51.7 mmol) and N-ethyl-methylamine (4.08 g, 69.0 mmol) is added. The mixture is stirred at rt for 45 min before NaBH(OAc)3 (8.12 g, 34.5 mmol) is added. The mixture is stirred at rt for 16 h before it is concentrated. The remaining residue is dissolved in MeCN and DMF and filtered over a paper filter. The filtrate is separated by prep. HPLC (Waters XBridge 50×50 mm+100×50 mm, eluting with a gradient of acetonitrile in water containing 0.5% of sat. aq. ammonia) to give the title compound as a white solid (1.67 g). LC-MS*: tR=0.46 min, [M−H]−=206.28; 1H NMR (D6-DMSO): δ 1.03 (t, J=7.3 Hz, 3H), 2.09 (s, 3H), 2.35 (s, 3H), 2.39 (q, J=7.0 Hz, 2H), 3.46 (s, 2H), 7.31 (s, 1H), 7.63 (s, 1H), 7.67 (s, 1H).

Provenance & Evidence