Methyl iodide → 6-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

HRID 1007204

Reaktionsgleichung

Reaktionsgleichung von HRID 1007204
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])=[O:9])=[CH:4][CH:3]=1.[CH3:23][O-].[Na+].IC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])[CH3:23])=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 98401276-Chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamideHCID 10942334Sodium Methoxide

Produkt 1

HCID 99022846-Chloro-N-(4-ethoxy-2-nitrophenyl)-N-methyl-3-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide (50 mg, 0.155 mmol) in DMF (2 ml) was added sodium methoxide (12 mg, 0.222 mmol) in DMF (1 ml) and the reaction mixture was stirred for 10 min. To the mixture was added iodomethane (22 mg, 0.155 mmol) slowly and the mixture was stirred for at room temperature for 3 h. It was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by column chromatography to yield the titled compound as a light brown liquid. 1H NMR (CDCl3): 8.17 (d, J=2.1, 1H), 7.68-7.65 (m, 1H), 7.35 (d, J=2.7, 1H), 7.21 (t, J=7.8, 2H), 7.10-7.06 (m, 1H), 4.08-4.01 (m, 2H), 3.40 (s, 3H), 1.44 (t, J=6.9, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred for at room temperature for 3 h
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2e9b5a0cb09742b5b398e9734a4ad3dd
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794397B2

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