Ethanol → Ethyl 6-chloronicotinate

HRID 1650182Notes

Reaction equation

HRID 1650182 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:11](O)[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH3:12])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 792226-Chloronicotinic acid

Product 1

HCID 2799611Ethyl 6-chloronicotinateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g dimethylaminopyridine, (0.03 mol), in 200 ml of methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and residue subjected to flash chromatography to give 16.7 g of the captioned compound as a low-melting white solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureto cool
  3. customsolvent removed in vacuo and residue

Sources & evidence

ORD record
ord-9bf4bc29e77c415db5c831bb15871820
Source dataset
uspto-grants-1990_05
Patent number
US04923884

Reaction notes

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