1-Fluoro-2-nitrobenzene → (4-Methyl-pyridin-3-yl)-(2-nitro-phenyl)-amine

HRID 80226

Reaktionsgleichung

Reaktionsgleichung von HRID 80226
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH2:18].F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27]>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:18][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27]

Komponenten

7

Edukt 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 1379353-Amino-4-picolineHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 12361028(4-Methyl-pyridin-3-yl)-(2-nitro-phenyl)-amineAusbeute 28,32 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

1M LiHMDS solution (9.25 mL, 9.25 mmol) in THF was added drop wise to a cooled solution of 4-Methyl-pyridin-3-ylamine (1 g, 9.25 mmol) in THF (10 mL) at 0° C. under nitrogen atmosphere. The resulting mixture was added drop wise to a solution of 1-fluoro-2-nitro-benzene (0.98 mL, 9.25 mmol) in THF at 0° C. The resulting reaction mass was stirred at room temperature overnight. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was diluted with ethyl acetate and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (50% ethyl acetate in hexane) to afford 600 mg of the product (28.32% yield).

Aufarbeitung

  1. customThe resulting reaction mass
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was purified by column chromatography on silica gel (50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9668a2ae2410479d8a21bac1ca13349d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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