Water → 3-(Azidomethyl)-2-methoxypyridine

HRID 1816606Notes

Reaction equation

HRID 1816606 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[CH:5][N:4]=1.C1(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)C=CC=CC=1.C12CCCCC1CCCNN=2.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:25]=[N+:26]=[N-:27])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 199401P,P-Diphenylphosphinic azideHCID 10630565(2-Methoxypyridin-3-yl)methanolHCID 66879275Diazabicyclo[5.4.0]undecene

Product 1

HCID 224939123-(Azidomethyl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.4 g of 2-methoxy-3-hydroxymethylpyridine was dissolved in 100 ml toluene, and 13.8 ml diphenyl phosphoryl azide and 9.5 ml diazabicyclo[5.4.0]undecene were added, and the mixture was stirred overnight at room temperature. Water was added to the reaction product which was then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 9.5 g of [(2-methoxy-3-pyridyl)methyl]azide.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ce86c1b95beb4a3ebd84d1468b145ddc
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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