Hydrochloric Acid → HCID 18987723, compound

HRID 2396585Notes

Reaction equation

HRID 2396585 reaction equation
P(Cl)(Cl)Cl.[ClH:5].[CH3:6][O:7][C:8](=[O:23])[C:9](Cl)([C:20]#[N:21])[CH2:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:12]=O>CN(C=O)C>[Cl:5][C:20]1[C:9]([C:8]([O:7][CH3:6])=[O:23])=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 18987720HCID 18987720, compound

Product 1

HCID 18987723HCID 18987723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

5 g of PCl3 were added to 25 mL of DMF at room temperature. The resulting yellow solution was saturated with anhydrous HCl while keeping the temperature below 90° C. 5 g (18 mmol) of methyl-2-chloro-2-cyano-4-phenyl-5-oxopentanoate in 5 mL DMF were added at 80° C. and the resulting solution heated at 90° C. for 90 min. The reaction mixture was cooled to room temperature, quenched with water, extracted with toluene, dried and distilled to give methyl 2-chloro-5-phenyl-3-pyridine carboxylate.

Workup

  1. customthe temperature below 90° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with toluene
  5. customdried
  6. distillationdistilled

Sources & evidence

ORD record
ord-d32c7f81ed8a4721a617071308ed88cc
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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