p-Fluoronitrobenzene → Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

HRID 2070303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070303
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([OH:11])[CH:10]=1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([O:11][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH:10]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 22040734Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The mixture containing methyl-5-hydroxypyridine-3-carboxylate (1 eq), Potassium bis(trimethylsilyl)amide (1.2 eq) was stirred in N,N-dimethylformamide for 2 hours at room temperature. To this mixture was added 1-fluoro-4-nitrobenzene (1.1 eq) and Potassium carbonate (1.2 eq) and stirred at 80° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate. MS: MH+=274.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate

Quellen und Nachweise

ORD-Eintrag
ord-7d128a329c344e9fa45c2d816f416480
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299108B2

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