Ethanol → Ethyl 6-chloronicotinate

HRID 6559

Reaction equation

HRID 6559 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-chloronicotinate

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 in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and the residue subjected to flash chromatography to give the title compound as a low-melting white solid. PMR (CDCl3): δ 1.44 (3H, t, J~6.2 Hz) 4.44 (2H, q, J~4.4 Hz), 7.44 (1H, d, J~8.1 Hz), 8.27 (1H, dd, J~8.1 Hz, 3 Hz), 9.02 (1H, d, J~3 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-8a817766383541e695f1bd93a0b40edf
Source dataset
uspto-grants-1993_09
Patent number
US05248777

Linked notes

Loading…