1,2-Dichloroethane → Methyl 6-methylpyridine-2-carboxylate

HRID 8209

Reaktionsgleichung

Reaktionsgleichung von HRID 8209
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.CO.[CH2:13](Cl)CCl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:13][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:10]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 887MethanolHCID 702826-Methylpyridine-2-carboxylic acid

Produkt 1

HCID 73022Methyl 6-methylpyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) in methylene chloride (200 mL) cooled to 0° C. is added methanol (10 mL), 4-dimethylaminopyridine (11.6 g, 94.8 mmol), and EDC (18.2 g, 94.8 mmol). The mixture is stirred at room temperature for 6 h, washed with water and brine, and dried over sodium sulfate. The mixture is filtered and concentrated in vacuo. The residue is chromatographed on SiO2 (50% ethyl acetate/hexanes) to yield the title compound, 9.66 g (92%), as a colorless liquid.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on SiO2 (50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6f91fd8aa044449a8fb53ad9db2adc17
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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