1-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetraazole → 3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)aniline
Reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([CH:13]=[CH2:14])[CH:10]=[C:9]([N+:15]([O-])=O)[CH:8]=2)=[N:5][N:4]=[N:3]1>CO.[OH-].[OH-].[Pd+2]>[CH2:13]([C:11]1[CH:10]=[C:9]([CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH:12]=1)[NH2:15])[CH3:14]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of impure 1-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetrazole (17.0 g) and palladium hydroxide on charcoal (3.0 g) in methanol (50 mL) was shaken under a hydrogen atmosphere (50 psig) for 4 hours. The mixture was filtered and the filtrate was concentrated under vacuum to provide an amber solid (14.3 g). 1H NMR (300 MHz, CDCl3) δ6.90 (s, 1H), 6.87 (s, 1H), 6.73 (s, 1H), 4.16 (s, 3H), 3.95 (bs, 2H), 2.65 (q, J=7 Hz, 2H), 1.22 (t, J=7 Hz, 3H).