Methanol → 4-Dimethylaminomethyl-2-hydroxymethylpyridine

HRID 1904075

Reaction equation

HRID 1904075 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:13][N:14]([CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[CH3:15].[CH3:23][OH:24].S(=O)(=O)(O)O>O>[CH3:13][N:14]([CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][OH:24])[CH:18]=1)[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 62648Ammonium PersulfateHCID 2649464-pyridinemethanamine, N,N-dimethyl-

Product 1

HCID 132926014-Dimethylaminomethyl-2-hydroxymethylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ammonium persulphate (102.7 g) in water (200 ml) was added over 40 minutes to a refluxing solution of 4-dimethylaminomethylpyridine (40.86 g), methanol (450 ml), water (210 ml) and concentrated sulphuric acid (30 ml). The resulting solution was refluxed for 2 hours, water (300 ml) was added and the methanol was distilled off. The cooled solution was basified and extracted with chloroform to give 4-dimethylaminomethyl-2-hydroxymethylpyridine (19.65 g) b.p. 92°-120°/0.06 mm Hg.

Workup

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. distillationthe methanol was distilled off
  3. extractionextracted with chloroform

Sources & evidence

ORD record
ord-c7eefca3e0a14bd684887e664777da8b
Source dataset
uspto-grants-1984_03
Patent number
US04439609

Linked notes

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