Thionyl Chloride → Ethyl chloronicotinate

HRID 2257515Notes

Reaction equation

HRID 2257515 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.O1CCO[CH2:17][CH2:16]1>C(O)C.O.C(N(CC)CC)C>[CH2:16]([O:5][C:4]([C:3]1[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:6])[CH3:17]

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 762582-Chloronicotinic acid

Product 1

HCID 2796614Ethyl chloronicotinateYield 90%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

10 g (0.0635 mole) of 2-chloronicotinic acid, 4.86 ml (0.067 mole) of thionylchloride and 30 ml of dioxane are heated at 70° C. for 3 hours. 20 ml of ethanol is added and the mixture is heated for 2 hours. After cooling to room temperature 10 ml of triethylamine, 10 ml of water and 5 ml ethanol is added. The solvents are evaporated and the residue is extracted with ether and water. The ether is evaporated and the crude product is isolated. The yield is 10.3 g (95%). Distillation of the crude product at 8 mm Bp. 122°-123° C. yielded 9.4 g (90%) of the title compound (2b:l), b.p. 122°-123° C. at 8 mm Hg.

Workup

  1. temperaturethe mixture is heated for 2 hours
  2. additionis added
  3. customThe solvents are evaporated
  4. extractionthe residue is extracted with ether and water
  5. customThe ether is evaporated
  6. customthe crude product is isolated
  7. distillationDistillation of the crude product at 8 mm Bp. 122°-123° C.

Sources & evidence

ORD record
ord-d7a438d30b7b4004aefba2570f4397ea
Source dataset
uspto-grants-1997_08
Patent number
US05658910

Reaction notes

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