Hydrochloric Acid → Ethyl chloronicotinate

HRID 2396575Notes

Reaction equation

HRID 2396575 reaction equation
CN(C=O)C.P(Cl)(Cl)Cl.[ClH:10].Cl[C:12]([C:22]#[N:23])([CH2:18][CH2:19][CH:20]=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1>[Cl:10][C:22]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=[CH:20][N:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 10998104Ethyl 2-chloro-2-cyano-5-oxopentanoate

Product 1

HCID 2796614Ethyl chloronicotinateYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of DMF (5.12 g, 70 mmol) in 80 mL of toluene were added 6.85 g of PCl3 (50 mmol). Anhydrous HCl was introduced for 5 min., keeping the temperature around 60° C. Ethyl 2-chloro-2-cyano-5-oxopentanoate (10.42 g, 50 mmol) in 20 mL of toluene was added in 30 minutes. The resulting mixture was stirred for 1 h at 80° C., cooled to room temperature, quenched with water, extracted with toluene, dried over MgSO4, and concentrated and distilled to give 5.5 g of the title compound (59%).

Workup

  1. customthe temperature around 60° C
  2. temperaturecooled to room temperature
  3. customquenched with water
  4. extractionextracted with toluene
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-116742283518487b85721fa1449b22bf
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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