Dimethylamine → 2-Dimethylaminomethyl-3-hydroxy-4-methylpyridine
Reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:9][NH:10][CH3:11].[CH2:12]=O>O>[CH3:9][N:10]([CH2:12][C:3]1[C:2]([OH:1])=[C:7]([CH3:8])[CH:6]=[CH:5][N:4]=1)[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution consisting of 3-hydroxy-4-methylpyridine (32.7 g.), 30% aqueous dimethylamine (46.5 ml.) and formalin (25 ml.) in water (50 ml.) was heated on a steam bath for a period of two hours. The cooled reaction solution was then extracted with ten-100 ml. portions of diethyl ether and the combined ether and extracts were subsequently dried over anhydrous magnesium sulfate and filtered. After removal of the volatile liquids by means of evaporation under reduced pressure, there was finally obtained an oil as residue which was subsequently distilled in vacuo to give pure 2-dimethylaminomethyl-3-hydroxy-4-methylpyridine (yield, 34.5 g.), b.p. 71°-74° C./0.6 mm. Hg. The corresponding dihydrochloride salt melted at 214°-217° C. (decomp.) after recrystallization from ethanol/diethyl ether.
Workup
- temperaturewas heated on a steam bath for a period of two hours
- customThe cooled reaction solution
- extractionwas then extracted with ten-100 ml
- dry with materialportions of diethyl ether and the combined ether and extracts were subsequently dried over anhydrous magnesium sulfate
- filtrationfiltered
- customAfter removal of the volatile liquids
- customby means of evaporation under reduced pressure, there
- customwas finally obtained an oil as residue which
- distillationwas subsequently distilled in vacuo
Sources & evidence
- ORD record
- ord-8dd41e8122944b6d8ab142ac3bc4b7ca
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04230714
Reaction notes
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