Tetrahydrofuran → 4-Chloro-N-methyl-3-nitropyridin-2-amine

HRID 1864670

Reaktionsgleichung

Reaktionsgleichung von HRID 1864670
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:14]1COCC1>>[Cl:11][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amine

Produkt 1

HCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amineAusbeute 25 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Amino-4-chloro-3-nitropyridine (590 mg, 4 mmol) was dissolved in dry THF (15 mL), the solution was cooled to 0° C. and NaH (240 mg, 6 mmol) was added. The reaction mixture was stirred for 2 hours, and allowed to warm at room temperature. The solvent was evaporated and the residue extracted between AcOEt and water. The organic layer was dried (MgSO4) and evaporated. The crude mixture was purified by column chromatography (eluent DCM) to afford the title compound (190 mg, 25%). 1H-NMR (6, ppm, DMSO-d6): 2.88 (d, 3H, Me, J=4.55 Hz), 6.86 (d, 1H, HPy,5, J=5.31 Hz), 7.44 (broad s, 1H, NH), 8.21 (d, 1H, HPy,5, J=5.30 Hz).

Aufarbeitung

  1. temperatureto warm at room temperature
  2. customThe solvent was evaporated
  3. extractionthe residue extracted between AcOEt and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography (eluent DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c2c06492e30a4a2eb9ed491907206444
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625922B2

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