Sodium Carbonate → 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine

HRID 707343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707343
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:15][CH:14]([NH2:16])[CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O.O>[N+:30]([C:29]1[C:24]([NH:16][CH:14]2[CH2:13][N:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:2]=3)[CH2:15]2)=[N:25][CH:26]=[CH:27][CH:28]=1)([O-:32])=[O:31]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 67477378HCID 67477378, Verbindung

Produkt 1

HCID 866942023-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(quinolin-2-yl)azetidin-3-amine hydrochloride (0.90 g, 3.84 mmol) in dry dimethylformamide (15 mL) was added sodium carbonate (1.22 g, 11.5 mmol) and 2-chloro-3-nitro-pyridine (608 mg, 3.84 mmol). The reaction mixture was stirred and heated at reflux for 14 hours. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL), and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether) to give 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine (1.05 g, 3.20 mmol, 85% yield) as yellow solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 14 hours
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with water (30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-06a561d50d1f4eaa86b271f8937d63e6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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