Iodoethane → Ethyl 4-chloropyridine-3-carboxylate

HRID 1984289Notes

Reaction equation

HRID 1984289 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[Na+].I[CH2:14][CH3:15]>CN(C)P(=O)(N(C)C)N(C)C.O>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:14][CH3:15])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 8182294-Chloronicotinic acid

Product 1

HCID 14116704Ethyl 4-chloropyridine-3-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 4-chloronicotinic acid (7.03 g, 44.6 mmol) in 100 mL of hexamethylphosphoric triamide (HMPA) was added a solution of 5.5 N sodium hydroxide (13 mL) at 0° C. Then iodoethane (27.8 g, 179 mmol) was added into the reaction mixture at 0° C. over 1 h, and stirring was continued for a further 1 h at room temperature. The mixture was diluted with 250 mL of water, and then extracted three times with ether. The ethereal extracts were combined, washed three times with water, then dried (MgSO4), filtered, and the solvent was evaporated to give ethyl 4-chloronicotinate (6.21 g) as a brown oily residue, which was used for the next step without further purification.

Workup

  1. extractionextracted three times with ether
  2. washwashed three times with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3765dee727464f2bbefeaec0fb30e0d2
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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