Dimethylformamide → 5-Butyl-2-chloro-nicotinic acid methyl ester

HRID 2100551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100551
O(Cl)[Cl:2].[CH3:4][O:5][C:6](=[O:16])/[C:7](/C#N)=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[N:18]([CH:20]=O)[CH3:19]>>[CH3:4][O:5][C:6](=[O:16])[C:7]1[CH:8]=[C:9]([CH2:10][CH2:11][CH2:12][CH3:13])[CH:20]=[N:18][C:19]=1[Cl:2]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24646Chlorine monoxideHCID 86616607(E)-2-cyano-oct-2-enoic acid methyl ester

Produkt 1

HCID 866166085-Butyl-2-chloro-nicotinic acid methyl esterAusbeute 17 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Phosporous oxychloride (4.76 ml, 51 mmol) was added within 10 minutes to an ice cold solution of (E)-2-cyano-oct-2-enoic acid methyl ester (4.65 g, 26 mmol) in DMF (12 ml) under an argon atmosphere. The reaction mixture was stirred for 14 h at 80° C. and poured onto ice water. After 3 h the mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water and dried over sodium sulfate. Removal of the solvent under reduced pressure left a brown oil which was purified by column chromatography (silica gel, isopropyl acetate/heptane) to give 5-butyl-2-chloro-nicotinic acid methyl ester (1.01 g, 4.4 mmol; 17%) as yellow oil. MS: m/e=227.0 [M+H+].

Aufarbeitung

  1. additionpoured onto ice water
  2. extractionAfter 3 h the mixture was extracted two times with dichloromethane
  3. washthe combined extracts were washed with ice water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. waitleft a brown oil which
  7. customwas purified by column chromatography (silica gel, isopropyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a067bf2053a04d929045bebf64a1c771
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572801B2

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