Dimethylformamide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

HRID 1831693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831693
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1Cl.[CH3:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1N(C)C.[C:29](=O)([O-])[O-].[K+].[K+].C[N:36]([CH:38]=O)C>[Cu]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[NH:36][C:38]1[C:25]([CH3:21])=[CH:26][C:27]([CH3:29])=[CH:28][C:20]=1[CH3:19]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11869N,N,2-TrimethylanilineHCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

Produkt 1

HCID 695872624-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

A mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester, trimethylaniline, potassium carbonate, copper in DMF was heated at reflux. The mixture was quenched with ammonium chloride and stirred for 20 min, filtered through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as a solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe mixture was quenched with ammonium chloride
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. extractionThe filtrate was extracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d5e7a9a6eae54bda89a9745297d04045
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067664B1

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