Oxalyl chloride → Methyl 2-(benzyloxy)-6-chloroisonicotinate

HRID 1096955Notes

Reaction equation

HRID 1096955 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[C:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]=1>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([O:16][CH3:1])=[O:15])[CH:11]=[C:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 27625082-Chloro-6-benzyloxypyridine-4-carboxylic acid

Product 1

HCID 57930944Methyl 2-(benzyloxy)-6-chloroisonicotinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalyst3×HCID 6212ChloroformSolvent

Procedure

With cooling with ice, oxalyl chloride (5.8 mL) and DMF (3 drops) were added to a CHCl3 (40 mL) solution of 2-chloro-6-benzyloxypyridine-4-carboxylic acid, and stirred at that temperature for 1 hour. DMF (3 drops) was added to it, and stirred overnight at room temperature, then oxalyl chloride (2.9 mL) and DMF (3 drops) were added to it, and stirred at room temperature for 3 hours. The solvent was evaporated away, CHCl3-MeOH was added to the residue, and stirred at room temperature for 30 minutes. Sodium bicarbonate water was added to the reaction solution, extracted with chloroform, and the organic layer was washed with water, saturated sodium bicarbonate water and saturated saline water, and dried with anhydrous sodium sulfate. This was filtered, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a yellow oil.

Workup

  1. stirringstirred overnight at room temperature
  2. stirringstirred at room temperature for 3 hours
  3. customThe solvent was evaporated away
  4. additionCHCl3-MeOH was added to the residue
  5. stirringstirred at room temperature for 30 minutes
  6. additionSodium bicarbonate water was added to the reaction solution
  7. extractionextracted with chloroform
  8. washthe organic layer was washed with water, saturated sodium bicarbonate water and saturated saline water
  9. dry with materialdried with anhydrous sodium sulfate
  10. filtrationThis was filtered
  11. concentrationconcentrated under reduced pressure
  12. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0a63c435e4e145fc96800427431caea7
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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