Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methoxy-4-ethyl-benzonitrile (13-2, 1.5 g, 9.31 mmol) in THF (45 mL) at 0° C. was added LAH (40 mL, 40.0 mmol) and stirred at 0° C. for 0.5 h. Quenched carefully over a period of 0.5 h with EtOAc at 0° C. and stirred for 15 minutes. Following this, water (1.5 mL) was added to this mixture and stirred for 15 minutes followed by 15% NaOH (1.5 mL) and again stirred for 15 minutes. Lastly, water (4.5 mL)was added and stirred for 15 more minutes. The mixture was dried over Mg2SO4, filtered and concentrated to yield a clear semi-solid. This semi-solid was treated with 2.0M HCl in ether (4.65 mL, 9.3 mmol) and the reaction contents were concentrated to afford the desired product as a white powder (13-3) in the form of a mono HCl salt. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 149.1 found, 149.2 required.

Provenance & Evidence