2-Chloronicotinic acid → 2-Ethoxynicotinic Acid

HRID 2407767Notes

Reaction equation

HRID 2407767 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>C(O)C>[CH2:2]([O:1][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])[CH3:3]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 2723922Sodium ethoxide

Product 1

HCID 27363452-Ethoxynicotinic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

A solution of sodium ethoxide (14.2 mL) was added to a solution of 2-chloronicotinic acid (2.00 g) in ethanol (13 mL). The mixture was heated in a sealed vessel at 170° C. for 2 days. After cooling, the mixture was concentrated in vacuo and the residue taken in water and acidified with hydrochloric acid to pH 3. The precipitated solids were collected by filtration and washed with water to obtain the title compound (1.32 g) having the following physical data.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-dc62b7633eaa408eb8d62e494388d43c
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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