[O-]CC.[K+].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([N:24]2[C:28]([CH3:29])=[N:27][N:26]=[N:25]2)=[C:17]([CH:23]=1)[C:18]([O:20]CC)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[Cl-].[NH4+]>CN(C=O)C>[CH2:5]([O:12][C:13]1[CH:23]=[C:17]2[C:16](=[CH:15][CH:14]=1)[N:24]1[N:25]=[N:26][N:27]=[C:28]1[CH:29]=[C:18]2[OH:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
Potassium ethoxide (57.5 g, 0.682 mol) was added portionwise to a solution of ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoate (115.6 g, 0.341 mol) in 550 mL of DMF. The reaction exothermed and the temperature increased by 35 degrees. The reaction mixture was cooled in an ice bath and stirred for 1 hour. The solution was then poured into 6 L of water containing 500 g of ammonium chloride. A yellow-orange precipitate formed. After stirring overnight, the reaction was filtered. The recovered solid was dried at 50° C. in a vacuum oven to provide 100 g of 7-(benzyloxy)tetraazolo[1,5-a]quinolin-5-ol.
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