Ethyl Acetate → HCID 22929783, compound

HRID 1295985Notes

Reaction equation

HRID 1295985 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:13][C:10]1[N:11]=[CH:12][C:7]([CH2:6][N:1]=[N+:2]=[N-:3])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 122143385-(Chloromethyl)-2-methylpyridine

Product 1

HCID 22929783HCID 22929783, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaN3 (11.2 g, 172 mmol) was added to a solution of the 5-(chloromethyl)-2-methylpyridine (12.2 g, 86.2 mmol) in dimethylformamide (120 ml) while cooling on ice and the mixture was stirred at the same temperature for 1 hour and then at room temperature for 2 hours. The reaction mixture was poured into semi-saturated aqueous sodium hydrogencarbonate, extraction was performed with ethyl acetate and the extract was washed with water and saturated aqueous NaCl. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (8.9 g, 26%, two steps) as a colorless oil.

Workup

  1. temperaturewhile cooling on ice
  2. waitat room temperature for 2 hours
  3. washthe extract was washed with water and saturated aqueous NaCl
  4. dry with materialAfter drying with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d63c1b9127834e9cbbadb639513381e5
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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