Triethylamine → Methyl 2-chloronicotinate

HRID 989907Notes

Reaction equation

HRID 989907 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:15](N(CC)CC)C>O1CCOCC1>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 819931Methyl 2-chloronicotinateYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-chloronicotinic acid (Aldrich, 100.0 g, 0.63 mol) in 1,4-dioxane (500 mL) was added thionyl chloride (70 mL, 0.96 mol). The suspension was heated under reflux for 22 h with a gas trap to absorb hydrogen chloride gas. After evaporation of the solvent, the residue was dissolved in methanol (300 mL). To the solution was added dropwise triethylamine (TEA, 120 mL, 1.26 mol) at 0° C. over 2 h. The solvents were evaporated and the residue was suspended in ethyl acetate. The precipitate was removed by filtration. The filtrate was concentrated to afford the ester 18 (92.3 g, 86%) as an oil:

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 22 h with a gas trap
  3. customto absorb hydrogen chloride gas
  4. customAfter evaporation of the solvent
  5. dissolutionthe residue was dissolved in methanol (300 mL)
  6. customThe solvents were evaporated
  7. customThe precipitate was removed by filtration
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-521f95f769ae4dcfa366d732d5b7cf9f
Source dataset
uspto-grants-2002_10
Patent number
US06458816B1

Reaction notes

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