2-Amino-5-methyl-7-pentafluoroethyl-1,8-naphthyridine → HCID 21428391, compound
Reaction equation
N[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:7][C:8]=2[CH3:12])[N:3]=1.N([O-])=[O:21].[Na+]>FC(F)(F)C(O)=O>[CH3:12][C:8]1[CH:7]=[C:6]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[N:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2](=[O:21])[NH:3]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-5-methyl-7-pentafluoroethyl-1,8-naphthyridine (5.54 g., 20 mmole) is dissolved in trifluoroacetic acid (40 ml.) and to the stirred solution cooled to -5° to 0° C. is added finely powdered sodium nitrite (3.0 g., 43.5 mmole) in small portions. Stirring of the mixture is continued at room temperature for one hour, after which it is poured into ice-water (ca. 500 ml.). The product precipitates and is collected, washed and dried at 60° C. in air. It can be purified by recrystallization from diisopropyl ether.