2-Chloronicotinic acid → 2-Ethoxynicotinic Acid

HRID 433948Notes

Reaction equation

HRID 433948 reaction equation
[K].[O-:2][CH2:3][CH2:4]CC.Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>C(O)C>[CH2:3]([O:2][C:8]1[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=[CH:15][N:16]=1)[CH3:4]

Participants

5

Reactant 3

HCID 762582-Chloronicotinic acidHCID 5462222PotassiumHCID 12476378Butan-1-olate

Product 1

HCID 27363452-Ethoxynicotinic AcidYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
170 °C

Procedure

A solution of potassium ten-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 ethanol (100 ml), and the reaction heated in a sealed vessel at 170° C. for 20 hours. The solvent was removed 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 combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound as a white solid (27.4 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water (200 ml)
  3. extractionThe aqueous solution was extracted with dichloromethane (4×200 ml)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2367d3a71e64e0c81acf5812d1d2d2f
Source dataset
uspto-grants-2003_12
Patent number
US06670366B1

Reaction notes

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