1-Iodopropane → 3-Methoxy-2-methyl-4-propoxypyridine

HRID 649208

Reaction equation

HRID 649208 reaction equation
[CH3:1][O:2][C:3]1[C:8](=[O:9])[CH:7]=[CH:6][NH:5][C:4]=1[CH3:10].[CH2:11](I)[CH2:12][CH3:13]>CN(C)C=O.C(Cl)(Cl)Cl.[Ag]=O>[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 2

HCID 336431-IodopropaneHCID 3234243-Methoxy-2-methyl-1H-pyridin-4-one

Product 1

HCID 139829483-Methoxy-2-methyl-4-propoxypyridine

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

3-Methoxy-2-methyl-4(1H)-pyridone(1.39 g) and propyl iodide (2.0 ml) were dissolved in dimethylformamide (20 ml), to which silver oxide (2.31 g) was added in small portions and stirred vigorously at room temperature for 5 hours. The reaction mixture was diluted with chloroform (100 ml), washed with water, dried and evaporated. The residue was purified by flash chromatography (chloroform) on silica gel, to give 3-methoxy-2-methyl-4-propoxypyridine (1.7 g) as a light brown oil.

Workup

  1. additionwas added in small portions
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash chromatography (chloroform) on silica gel

Sources & evidence

ORD record
ord-2a493dc1dce0447e91aa00ee831790d4
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Linked notes

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