Ethanol → Ethyl 4-chloropyridine-3-carboxylate

HRID 1819387Notes

Reaction equation

HRID 1819387 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH:11]1(N=C=NC2CCCCC2)CCCC[CH2:12]1.CCO>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:11]([O:9][C:8](=[O:10])[C:7]1[C:2]([Cl:1])=[CH:3][CH:4]=[N:5][CH:6]=1)[CH3:12]

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 8182294-Chloronicotinic acid

Product 1

HCID 14116704Ethyl 4-chloropyridine-3-carboxylateYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-nicotinic acid (2.5 g, 15.9 mmol) in DMF (26 mL)), were added Dicyclo-hexylcarbodiimide (DCC) (7.75 g, 37.5 mmol), 4-dimethylaminopyridine (DMAP) (0.286 g, 2.1 mmol) and EtOH (2.6 mL, 46.8 mmol). The reaction mixture was stirred at room temperature for 4 h. The mixture was then distilled (0.1 mmHg) to afford 1.5 g (51%) of 4-chloro-nicotinic acid ethyl ester as a colorless oil.

Workup

  1. distillationThe mixture was then distilled (0.1 mmHg)

Sources & evidence

ORD record
ord-a97e64e16b2c4a209cd0df11db0bae4e
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…