Toluene → Methyl4-[4-(methylamino)-3-nitrophenoxy]pyridine-3-carboxylate

HRID 2070305

Reaktionsgleichung

Reaktionsgleichung von HRID 2070305
COC([C:5]1C=N[CH:8]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)C(F)(F)F)=[C:14]([N+:25]([O-:27])=[O:26])[CH:13]=2)[CH:10]=1)=O.[C:28](#[N:30])C.[OH-:31].[Na+].S(OC)([O:36][CH3:37])(=O)=O.[C:40]1(C)C=CC=CC=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH3:40][O:31][C:37]([C:8]1[CH:28]=[N:30][CH:5]=[CH:10][C:9]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH3:19])=[C:14]([N+:25]([O-:27])=[O:26])[CH:13]=1)=[O:36]

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 6342AcetonitrileHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 22040901Methyl5-[3-nitro-4-(2,2,2-trifluoroacetylamino)phenoxy]-pyridine-3-carboxylate

Produkt 1

HCID 22040570Methyl4-[4-(methylamino)-3-nitrophenoxy]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5963Benzyltrimethylammonium chlorideKatalysator

Versuchsvorschrift

To the solution of the methyl5-[3-nitro-4-(2,2,2-trifluoroacetylamino)phenoxy]-pyridine-3-carboxylate (1 eq) in a mixture of toluene, acetonitrile and sodium hydroxide solution (50%) was added benzyltrimethylammonium chloride (1 eq) and dimethyl sulfate (1.2 eq). The biphasic mixture was stirred overnight at room temperature and evaporated. The mixture was taken up in ethyl acetate, washed with water, brine, dried and evaporated. The crude was purified by column chromatography to afford methyl4-[4-(methylamino)-3-nitrophenoxy]pyridine-3-carboxylate. MS: MH+=303.

Aufarbeitung

  1. customevaporated
  2. washwashed with water, brine
  3. customdried
  4. customevaporated
  5. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6d96a6a165674f7496c0524039b32279
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299108B2

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