Pyridine → n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide

HRID 558090

Reaktionsgleichung

Reaktionsgleichung von HRID 558090
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:6]([C:5]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[C:4]=2[N+:16]([O-:18])=[O:17])=[O:8])=[N:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 706222-Amino-5-bromopyridineHCID 971163,4,5-Trimethoxy-2-nitrobenzoic acid

Produkt 1

HCID 22596319n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

_To a solution of 3,4,5-trimethoxy-2-nitrobenzoic acid (0.5 g, 1.95 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.34 ml, 3.9 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-bromopyridine (0.81 g, 4.7 mmol) and pyridine (0.94 ml, 11.7 mmol) were added to the solution. The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-(5-bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide as a solid (790 mg; 98%). MS found for C15H14BrN3O6 M+=412, (M+2)+=414.

Aufarbeitung

  1. customAfter the evaporation of the solvent
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at r.t. overnight
  4. customAfter the evaporation of the solvent
  5. customthe crude residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1895e39548da48be9c29378e1f178a88
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063036B2

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