Pyridine → N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide

HRID 44236

Reaktionsgleichung

Reaktionsgleichung von HRID 44236
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[Cl:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1.N1C=CC=CC=1>O1CCCC1.O>[Cl:14][C:15]1[C:20]([NH:21][C:7](=[O:8])[C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=[CH:17][N:16]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 805282-Chloro-3-pyridylamineHCID 30160135-Methyl-2-nitrobenzoyl chloride

Produkt 1

HCID 3440161N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamideAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5-methyl-2-nitrobenzoyl chloride (3.77 g, 18.9 mmol) in tetrahydrofuran (25 mL) was treated with a solution consisting of 2-chloropyridin-3-amine (2.6 g, 20.22 mmol), pyridine (6 mL) and tetrahydrofuran (15 mL). The reaction mixture was stirred for 2 hours then diluted with water (150 mL) and extracted with dichloromethane (3×70 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (100 mL) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide (5.44 g) that was used without further purification. LCMS [M+H]: 292.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×70 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8de85d599504467eb920c5fc0f296886
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541407B2

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