Reaction #75730

Reaction equation

Ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate

N,N-dimethylformamide

potassium ethoxide

→

tetrazolo[1,5-a][1,8]naphthyridin-5-ol

Yield 89.1%

Solvents

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe resulting precipitate was isolated by filtration
3. 3
   Washwashed with water
4. 4
   Otherthen dried

Procedure

Ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate (6.3 g, 27 mmole) was covered with N,N-dimethylformamide (50 mL), potassium ethoxide (4.5 g, 54 mmole) was added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into ice water containing about 17 mL of acetic acid. The resulting precipitate was isolated by filtration, washed with water then dried to provide 4.5 g of tetrazolo[1,5-a][1,8]naphthyridin-5-ol as an off white solid, m.p. 236° (decomposition). Analysis: Calculated for C8H5N5O: %C, 51.34; %H, 2.69; %N, 37.42. Found: %C, 51.23; %H, 2.77; %N, 37.25.

Source