Water → Methyl 2-chloronicotinate

HRID 130343

Reaktionsgleichung

Reaktionsgleichung von HRID 130343
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 819931Methyl 2-chloronicotinateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-54e1d1195258426687008a009f96fe02
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381734B2

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