Oxalyl chloride → 2-Benzoyl-6-methylpyridine

HRID 27707

Reaction equation

HRID 27707 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(=O)[C:12](Cl)=O>C1C=CC=CC=1>[C:8]([C:6]1[N:7]=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=1)(=[O:10])[C:12]1[CH:11]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 702826-Methylpyridine-2-carboxylic acid

Product 1

HCID 126232682-Benzoyl-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

To 15 g of 6-methyl-2-pyridylcarboxylic acid (122 mmol) in 200 ml benzene is added dropwise 19.1 g (150 mmol) oxalyl chloride (dissolved in 30 ml benzene) with ice bath cooling. The solution is allowed to come to RT and is stirred 1 hour, after which it is stripped, 100 ml of benzene is added, and it is stripped again. The residue is taken up in 200 ml benzene and 41 g of aluminumtrichloride (310 mmol) is added in portions over a 3 hour period with ice bath cooling. The solution is heated to 25° for 1 hour, then heated to reflux for 2 hours, and finally cooled and stirred overnight. The mixture is poured onto ice/conc. HCl, then washed with ether. Fifty Percent (50%) sodium hydroxide is added until the precipitate is dissolved. The solution is extracted with CHCl3, washed with water, dried and stripped, leaving 6-benzoyl-2-methylpyridine.

Workup

  1. temperaturecooling
  2. customto come to RT
  3. addition41 g of aluminumtrichloride (310 mmol) is added in portions over a 3 hour period with ice bath
  4. temperaturecooling
  5. temperatureThe solution is heated to 25° for 1 hour
  6. temperatureheated
  7. temperatureto reflux for 2 hours
  8. temperaturefinally cooled
  9. stirringstirred overnight
  10. additionThe mixture is poured onto ice/conc
  11. washHCl, then washed with ether
  12. additionFifty Percent (50%) sodium hydroxide is added until the precipitate
  13. dissolutionis dissolved
  14. extractionThe solution is extracted with CHCl3
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-c4eb971eb70b4c42af88f7786086da5f
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Linked notes

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