Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH2:20][NH2:21].[N:22]([O-])=O.[Na+]>O.C(O)(=O)C>[CH3:18][C:16]([CH3:19])([OH:17])[CH2:15][N:14]1[C:10]2[C:9]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:20]3[N:21]=[N:22][N:3]=[C:2]3[C:11]=2[N:12]=[CH:13]1
A suspension of 4-chloro-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (1.0 g, 3.6 mmole, U.S. Pat. No. 4,689,338 Example 189 Part D) in hydrazine (3 mL, 6.9 mmole) was heated on a steam bath for 1 hour then diluted with water. The resulting precipitate was isolated by filtration. The solid was dissolved in a mixture of acetic acid (2 mL) and water (15 mL) then combined with a solution of sodium nitrite (0.5 g) in water. The resulting precipitate was isolated by filtration, washed with water and dried to provide 0.71 g of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol as a white solid, m.p. 246-247° C. (shrunk at 230° C.). Analysis: Calculated for C14H14N6O: %C, 59.56; %H, 5.00; %N, 29.77; Found: %C, 59.45; %H, 5.06; %N, 29.51.
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