Reaction #75738

Reaction equation

Potassium ethoxide

ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate

dimethylformamide

→

tetrazolo[1,5-a][1,7]naphthyridin-5-ol hydrate

Yield 90.9%

Solvents

acetic acid

Conditions

Workup

1. 1
   OtherThe resulting precipitate was collected
2. 2
   Washwashed with water
3. 3
   Otherdried

Procedure

Potassium ethoxide (20.2 g) was added to a mixture of ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate (28 g) and dimethylformamide (280 mL). The reaction mixture was allowed to stir at ambient temperature overnight then poured into cold dilute acetic acid. The resulting precipitate was collected, washed with water and dried to provide 22.4 g of tetrazolo[1,5-a][1,7]naphthyridin-5-ol hydrate as a solid, m.p. 247-248° C. (decomposition). Analysis: Calculated for C8H5N5O: %C, 46.83; %H, 3.44; %N, 34.13. Found: %C, 46.48; %H, 3.42; %N, 34.03.

Source