[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:25][OH:26].OS(O)(=O)=O>O>[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[CH:9][N:10]=[C:11]([CH2:25][OH:26])[CH:12]=1)[CH2:4][CH3:5])[CH3:2]Treatment of 4-(N,N-diethylaminomethyl)pyridine (2.0 g, 12.20 mmol) with ammonium persulfate (5.56 g, 24.4 g, 2.0 equiv.), methanol (22 ml), water (11 ml) and concentrated H2SO4 (2.76 g, 28.18 mmol, 2.31 equiv.) as described for Cpd #214 gave 0.697 g (29%) of 4-(N,N-diethylaminomethyl)-2-hydroxymethylpyridine.
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