Potassium Hydroxide → 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine

Participants

Reaction Steps

To a stirred solution of 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide (19.7 g, 48.3 mmol, 1 eq.) in 200 ml of ethanol, was added potassium hydroxide (88.4 g, 1.57 mol, 32.6 eq.). The reaction mixture was stirred and heated to reflux for 4 hrs. After evaporation of the solvent, The residue was taken up with water (300 ml) and extracted with EtOAc (100 ml). The aqueous layer was separated and extracted twice with EtOAc (100 ml). The organics were combined, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine (10.7 g, 90% pure, 61% yield)

Provenance & Evidence