Potassium Carbonate → Methyl 6-(chloromethyl)pyridine-2-carboxylate

HRID 520477

Reaktionsgleichung

Reaktionsgleichung von HRID 520477
O=S(Cl)[Cl:3].O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Produkt 1

HCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylateAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

SOCl2 (57 g, 0.48 mol) was added to a solution of methyl 6-(hydroxymethyl)picolinate 66 (40.0 g, 0.239 mol) (Chem. Eur. J. 2006, 12, 6393-6402) in dichloromethane (500 mL) at room temperature. The mixture was stirred at 40° C. for 1 h and sat. aq K2CO3 was added to adjust the pH to 9. The mixture was extracted with CH2Cl2 and the combined organics were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 67 (45 g).

Aufarbeitung

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3040965c9beb4b7faa1e882259a44048
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326986B2

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