ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate → HCID 178515414, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate (92.7 g, 0.34 mol) was dissolved in N,N-dimethylformamide (600 ml) and the solution was chilled in an ice water bath. Potassium ethoxide (67.2 g, 0.80 mol) was added slowly to the solution. After a few minutes, the ice water bath was removed and the reaction was stirred at room temperature for 3 hours. The reaction was treated with 100 ml of water and approximately 300-400 ml of solvent was removed in vacuo. The remainder of the reaction was poured over a solution of glacial acetic acid (125 ml) in ice water (2 L). A precipitate formed and the mixture was diluted with additional water (3 L). The solid was collected by vacuum filtration to yield 63.25 g of tetrazolo[1,5-a]quinolin-5-ol as a yellow solid.

Provenance & Evidence