Hydrochloric Acid → Ethyl chloronicotinate

HRID 2396576Notes

Reaction equation

HRID 2396576 reaction equation
P(Cl)(Cl)Cl.[ClH:5].Cl[C:7]([C:17]#[N:18])([CH2:13][CH2:14][CH:15]=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>CN(C=O)C>[Cl:5][C:17]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=[CH:15][N:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 10998104Ethyl 2-chloro-2-cyano-5-oxopentanoate

Product 1

HCID 2796614Ethyl chloronicotinateYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To 35 mL of DMF were added dropwise 6.85 g of PCl3 (50 mmol). Anhydrous HCl was introduced for 5 minutes while keeping the temperature around 70° C. Ethyl 2-chloro-2-cyano-5-oxopentanoate (7.83 g, 38.5 mmol) in 10 mL of DMF was added at 55° C. The resulting mixture was stirred for 2 h at 90° C., cooled to room temperature, quenched with water, extracted with CH2Cl2, dried over MgSO4, concentrated and distilled to give 4.4 g of the title compound (62%).

Workup

  1. customthe temperature around 70° C
  2. temperaturecooled to room temperature
  3. customquenched with water
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-5980dabe74d946b8ab7c1d3f288bf017
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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