2-Chloronicotinic acid → 2-Ethoxynicotinic Acid

HRID 990244Notes

Reaction equation

HRID 990244 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 2-chloronicotinic acid (30 g, 0.19 mol) in absolute ethanol (100 ml) and the reaction mixture heated in a sealed vessel at 170° C. for 20 hours, then allowed to cool. The resulting mixture was evaporated under reduced pressure, the residue dissolved in water (200 ml) and the solution acidified to pH 3 with hydrochloric acid and extracted with dichloromethane (4×200 ml). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure to give the title compound (27.4 g, 41%) as a white solid. δ (CDCl3): 1.53 (3H, t), 4.69 (2H, q), 7.13 (1H, m), 8.37 (1H, d), 8.48 (1H, d).

Workup

  1. temperatureto cool
  2. customThe resulting mixture was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in water (200 ml)
  4. extractionextracted with dichloromethane (4×200 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba095f281af44f1d9191ad3b804215a9
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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