Dimethyl Sulfoxide → 2-Chloro-4-pyridinecarboxaldehyde

HRID 1740660Notes

Reaction equation

HRID 1740660 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 27629942-Chloro-4-pyridinecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (42.2 ml) in methylene chloride (1100 ml) is added dropwise a solution of dimethyl sulfoxide (68.7 ml) in methylene chloride (220 ml) at -60° C. to -50° C., and thereto is further added dropwise a solution of 2-chloro-4-hydroxymethylpyridine (63.2 g) in methylene chloride (440 ml) at the same temperature. The mixture is stirred for 15 minutes, and thereto is added dropwise triethylamine (306.6 ml) at the same temperature. The mixture is stirred for five minutes, and warmed to room temperature. After the reaction is complete, to the reaction mixture is added water (2.2 liters). The methylene chloride layer is separated, and the aqueous layer is extracted again with methylene chloride (2.2 liters). The methylene chloride layers are combined, and washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and concentrated under reduced pressure to remove the solvent to give 2-chloropyridine-4-carbaldehyde.

Workup

  1. stirringThe mixture is stirred for five minutes
  2. customThe methylene chloride layer is separated
  3. extractionthe aqueous layer is extracted again with methylene chloride (2.2 liters)
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-523607ced96047ca86aa9c8be1fcd609
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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