Ethanol → Ethyl 3-pyridylacetate

HRID 536170Notes

Reaction equation

HRID 536170 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:3]=1.S(=O)(=O)(O)O.[OH-].[NH4+].[CH2:19](O)[CH3:20]>>[CH2:19]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)[CH3:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)

Product 1

HCID 96490Ethyl 3-pyridylacetate

Procedure

To a solution of 3-pyridylacetic acid hydrochloride (40 g, 230.41 mmol) in ethanol (90 mL) was added sulfuric acid (73 g, 744.3 mmole, 98%) under N2. The reaction mixture was refluxed for 4 h, then cooled to rt. Ammonium hydroxide (250 mL, 25%) was added and extracted with DCM (500 mL) twice, dried over sodium sulfate, concentrated to afford the title product (33 g),

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. extractionextracted with DCM (500 mL) twice
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d90bed7f1274cdc9941c8ccd1b71cce
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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