Oxalyl chloride → 2-Chloronicotinoyl chloride

HRID 2294130Notes

Reaction equation

HRID 2294130 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 27745412-Chloronicotinoyl chlorideYield 38,976.398%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloronicotinic acid (20 g, 0.127 mmol) and oxalyl chloride (13.3 mL, 0.152 mmol) in 2 drops of DMF and 200 mL of methylene chloride was stirred at room temperature for approximately 14 hours. The mixture was stirred at reflux temperature for 1 hour. The solution was cooled and partitioned between 100 mL of ice-cold aqueous sodium bicarbonate and 300 mL of methylene chloride. The organic layer was washed with brine, dried (Na2SO4) and concentrated to give 2-chloronicotinic acid chloride (8.8 g, 49.5 mmol).

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux temperature for 1 hour
  3. temperatureThe solution was cooled
  4. custompartitioned between 100 mL of ice-cold aqueous sodium bicarbonate and 300 mL of methylene chloride
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca306e68a37b46eead879f2807df420b
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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