Methyl iodide → Methyl 2-chloro-6-methylpyridine-3-carboxylate

HRID 62847

Reaktionsgleichung

Reaktionsgleichung von HRID 62847
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CI.[C:14]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1217242-Chloro-6-methylnicotinic acid

Produkt 1

HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Chloro-6-methyl-nicotinic acid (3.58 g, 20.86 mmol) was dissolved in DMF (34 mL). MeI (5.8 mL, 93.88 mmol) and K2CO3(7.78 g, 56.33 mmol) were added thereto, and the mixture was stirred at room temperature for 2 hours. The reactant was distilled under reduced pressure to remove the solvent and extracted with EtOAc. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/2) to obtain the title compound (3.68 g, 94%).

Aufarbeitung

  1. distillationThe reactant was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-fbfad6ac0e674b76aae3f5c4101743e1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447044B2

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