Acetic Acid → METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATE

HRID 2177658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177658
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1Cl.[Na].[C:14](O)(=[O:16])C>CO.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[O:16][CH3:14]

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 5360545Sodium2×HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

Produkt 1

HCID 10910170METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATE

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-chloro-6-methyl-nicotinic acid methyl ester (10.4 g, 56.52 mmol) in MeOH under nitrogen is added a solution of sodium (2.58 g, 113.04 mmol) in methanol (80.0 mL) (sodium metal is dissolved in methanol under a nitrogen atmosphere) at room temperature. The reaction mixture is refluxed overnight. The reaction is cooled to room temperature and the pH is adjusted to pH=7 with acetic acid. The reaction mixture is diluted with ethyl acetate (100 mL) and water (30 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×75 mL). The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give crude product. Yield: 7.25 g (71%). 1H NMR (400 MHz, CDCl3), δ8.066-8.047 (d, J=7.6 Hz, 1H), 6.782-6.764 (d, J=7.2 Hz, 1-1H), 4.029 (s, 3H), 3.879 (s, 3H), 2.483 (s, 3H); ES/MS m/z 182.2 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed overnight
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (2×75 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product

Quellen und Nachweise

ORD-Eintrag
ord-aaa03f6945f040bca35bd6002d079408
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067920B2

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