Pyridine → N-(5-chloropyridin-2-yl)-2-nitrobenzamide

HRID 1247136

Reaktionsgleichung

Reaktionsgleichung von HRID 1247136
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16]>ClCCl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[N+:15]([O-:17])=[O:16])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 661742-Amino-5-chloropyridine

Produkt 1

HCID 766647N-(5-chloropyridin-2-yl)-2-nitrobenzamideAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-amino-5-chloropyridine (3.7 g, 29 mmol) and pyridine (7.3 mL, 90 mmol) in dichloromethane was added 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After stirring for 4 h, the solvents were removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. After standing at room temperature overnight, the mixture was filtered to give 6.4 g (79%) of a white solid.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. waitAfter standing at room temperature overnight
  8. filtrationthe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-fb969452a7824d4d87b294b4c0670fec
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129245B2

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