2-Chloronicotinic acid → 2-Ethoxynicotinic Acid

HRID 2271052Notes

Reaction equation

HRID 2271052 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>C(O)C>[CH2:2]([O:4][C:8]1[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=[CH:15][N:16]=1)[CH3:1]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 27363452-Ethoxynicotinic AcidYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
170 °C

Procedure

A solution of potassium t-butoxide (44.9 g, 0.40 mol) in absolute ethanol (300 ml) was added slowly to a solution of 2chloronicotinic acid (30 g, 0.19 mol) in ethanol (100 ml), and the reaction heated in a sealed vessel at 170° C. for 20 hours. On cooling, the reaction mixture was concentrated under reduced pressure, the residue dissolved in water (200 ml) and acidified to pH 3 with aqueous hydrochloric acid. The aqueous solution was extracted with dichloromethane (4×200 ml), the organic phases combined, dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (27.4 g, 41%) as a white solid.

Workup

  1. temperatureOn cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in water (200 ml)
  4. extractionThe aqueous solution was extracted with dichloromethane (4×200 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34084d1cffa14baaa7c8c26375176385
Source dataset
uspto-grants-2001_12
Patent number
US06333330B1

Reaction notes

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