Ethanol → Ethyl 5-Chloropyridine-2-carboxylate

HRID 1289761Notes

Reaction equation

HRID 1289761 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#N)=[N:6][CH:7]=1.Cl.[CH2:11]([OH:13])[CH3:12].C([OH:16])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:13][CH2:11][CH3:12])=[O:16])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 38339425-Chloro-2-cyanopyridineHCID 21887872Ethanol hydrochloride

Product 1

HCID 15414989Ethyl 5-Chloropyridine-2-carboxylateYield 97%

Procedure

To a solution of the compound (3.16 g) obtained in (2) above in ethanol (5 ml) was added a 2.7N hydrochloric acid-ethanol solution (10 ml) and the mixture was stirred with refluxing for 2 hours. Ethanol was distilled away under reduced pressure, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was dried over magnesium sulfate and the solvent was distilled away under reduced pressure to give 4.10 g of a pale-brown solid (yield 97%).

Workup

  1. temperaturewith refluxing for 2 hours
  2. distillationEthanol was distilled away under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-a75f1d18752644c2af8c0857a7368a03
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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