Water → Methyl 2-chloronicotinate

HRID 1830526Notes

Reaction equation

HRID 1830526 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(=O)(=O)(O)O.O.[C:17]([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 762582-Chloronicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 819931Methyl 2-chloronicotinateYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloronicotinic acid (1.61 g, 10.2 mmol) and sulfuric acid (0.5 mL) in methanol (30 mL) was stirred at reflux overnight. The solution was poured into water (100 mL) and neutralised with NaHCO3 (s) before being extracted with 1:1 hexane/ethyl acetate (3×40 mL). The solvents were dried (MgSO4) and evaporated and the residue was purified by flash column chromatography (SiO2, 25% ethyl acetate/hexane eluent) to afford the ester as a colourless oil (700 mg, 40%).

Workup

  1. temperatureat reflux overnight
  2. extractionbefore being extracted with 1:1 hexane/ethyl acetate (3×40 mL)
  3. dry with materialThe solvents were dried (MgSO4)
  4. customevaporated
  5. customthe residue was purified by flash column chromatography (SiO2, 25% ethyl acetate/hexane eluent)

Sources & evidence

ORD record
ord-8f329f2f01184bcda70aba4796b0d888
Source dataset
uspto-grants-2006_06
Patent number
US07067516B2

Reaction notes

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