Hydrochloric Acid → 2-Chloro-5-(chloromethyl)pyridine

HRID 484217Notes

Reaction equation

HRID 484217 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[ClH:7].Cl[C:9]([CH2:16][Cl:17])([CH2:12][CH2:13][C:14]#[N:15])[CH:10]=O>CN(C=O)C>[Cl:7][C:14]1[CH:13]=[CH:12][C:9]([CH2:16][Cl:17])=[CH:10][N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 10932027HCID 10932027, compound

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a three necked, 100-mL round bottom equipped with a reflux condenser, gas inlet tube and a thermometer was charged 50 mL of N,N-dimethylformamide. Phosphorous pentachloride (2.3 g, 11 mmol) was added in several portions and anhydrous hydrogen chloride was introduced slowly. The reaction temperature was kept around 60° C.-85° C. by means of a water bath. 2-Chloro-2-chloromethyl-4-cyanobutyraldehyde in 5 mL of DMF was added at 80° C., through a syringe pump within a period of 1 h. The resulting mixture was then heated to 100° C. under stirring for 8 h, quenched with water, neutralized using NaHCO3 to a pH of 5, extracted with methylene chloride, dried over MgSO4, and concentrated and distilled to give 0.5 g of 2-chloro-5-chloromethylpyridine. Purity by GLC analysis was 95%.

Workup

  1. customTo a three necked, 100-mL round bottom equipped with a reflux condenser, gas inlet tube
  2. additionwas introduced slowly
  3. customThe reaction temperature was kept around 60° C.-85° C. by means of a water bath
  4. customquenched with water
  5. extractionextracted with methylene chloride
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-4dcf3f1965e1435697e1363ac0d731b3
Source dataset
uspto-grants-1993_07
Patent number
US05229519

Reaction notes

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