Ethanol → Ethyl 3-chloroisonicotinate

HRID 1508196Notes

Reaction equation

HRID 1508196 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][CH2:12]O>OS(O)(=O)=O>[CH2:11]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[Cl:1])[CH3:12]

Participants

4

Reactant 2

HCID 702EthanolHCID 27358163-Chloropyridine-4-carboxylic acid

Product 1

HCID 2762498Ethyl 3-chloroisonicotinate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-chloroisonicotinic acid (18.6 mmol) in 120 mL EtOH and 3 mL conc. H2SO4 was heated to reflux overnight. The mixture was concentrated in vacuo, redissolved in aq. NaHCO3 solution and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as yellow oil;

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionredissolved in aq. NaHCO3 solution
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-705167690877422d912cde74f65b8ce1
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

Loading…