P-Anisidine → 6-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide

HRID 889322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889322
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:28])=O>>[Cl:28][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:8])=[CH:4][N:3]=1

Komponenten

5

Edukt 4

HCID 7732P-AnisidineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 2389326-Bromonicotinic acid

Produkt 1

HCID 14832696-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide

Versuchsvorschrift

6-Bromonicotinic acid (200 mg, 0.99 mmol) was heated at reflux in thionyl chloride (2 ml) for 3 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in DCM (2 ml), p-anisidine (123 mg, 0.10 mmol) and sodium carbonate (500 mg) were added to the solution. The reaction was stirred at room temperature for 4 hrs, filtered and the filtrate reduced to dryness under vacuum to give 6-chloro-N-(4-methoxyphenyl)nicotinamide. NMR: δH [2H6]-DMSO 10.37,(1H, b), 8.94,(1H, d), 8.34,(1H, dd), 7.70,(1H, d), 7.66,(2H, m), 6.95,(2H, m), 3.75,(3H, s).

Aufarbeitung

  1. customthe excess thionyl chloride evaporated under vacuum
  2. dissolutionThe residue was dissolved in DCM (2 ml)
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-58f9ce90e92141b2b631efa48ae62d99
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252818B2

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