Hydrochloric Acid → HCID 19832002, compound

HRID 2051501Notes

Reaction equation

HRID 2051501 reaction equation
Cl[C:2]1[CH:7]=[C:6](C(=O)C)[CH:5]=[CH:4][N:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22]([OH:24])[CH3:23]>O>[C:22]([C:2]1[N:3]2[N:11]=[N:12][N:13]=[C:4]2[CH:5]=[CH:6][CH:7]=1)(=[O:24])[CH3:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 33557Sodium Azide2×HCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 19832002HCID 19832002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11.42 g of 2-chloro-4-acetylpyridine, 9.51 g of sodium azide and 9.2 ml of 12 N HCl in 86 ml of a 1:1 ethanol:water mixture was heated at reflux for three hours. An additional 9.2 g of sodium azide was added and the reaction mixture heated at reflux overnight. An aqueous solution of sodium carbonate (3.92 g) was added and the mixture repeatedly extracted with methylene chloride. The combined extracts were washed with water and saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. Concentration under reduced pressure afforded 10.2 g of product.

Workup

  1. temperatureat reflux for three hours
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux overnight
  4. extractionthe mixture repeatedly extracted with methylene chloride
  5. washThe combined extracts were washed with water and saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-280dc36db2564c0d90b1d08376102d97
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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