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

HRID 1915680

Reaktionsgleichung

Reaktionsgleichung von HRID 1915680
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 methyl-4-[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-1746b7f8497d49da82250363abb679c8
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614330B2

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