Sodium borohydride → Amino(pyridin-3-yl)acetonitrile
Reaction equation
[BH4-].[Na+].[I-].C(O[C:9]1[C:10]([C:14]2[CH:15]=[N+:16](C)[CH:17]=[CH:18][CH:19]=2)=[N:11]S[N:13]=1)CCC>C(O)C>[NH2:11][CH:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:9]#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium borohydride (240 mg, 6.4 mmol) was added to a solution of 3-(4-butoxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide (0.60 g, 1.6 mmol) in ethanol (99.9%, 20 ml) and the reaction mixture was stirred at 0° C. for 1 h. After evaporation the residue was dissolved in water and extracted with ethyl acetate. The dried organic phases were evaporated and the residue purified by column chromatography (SiO2, eluent: ethyl acetate/methanol (4:1)). The title compound was crystallized as the oxalate salt from acetone to yield 280 mg (M.p 158° C.; M+ : 253; Compound 4).