Sodium borohydride → 4-(2-Hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine
Reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[N+:8]([O-])=[C:9]([CH3:11])[CH:10]=1.[BH4-].[Na+]>CO.[Pd]>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[CH:6]=1Participants
5
Procedure
4-(2-hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine-N-oxide (23) (2.40 g, 9.22 mmoles) was dissolved in methanol (75 ml). 10% palladium on carbon (0.54 g) was added and then slowly sodium borohydride (3.24 g, 85.6 mmoles). Palladium on carbon was filtered out and the solvent was evaporated. The product was purified by means of flash chromatography (silica, 5-50% methanol/chloroform).