Acetic Acid → 5-Iodo-N,N-dimethylpyridin-2-amine

HRID 1350687

Reaktionsgleichung

Reaktionsgleichung von HRID 1350687
NC1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[H-].[Na+].IC.CC(O)=O.[CH3:17][N:18]([CH:20]=O)[CH3:19]>CCOC(C)=O>[I:8][C:5]1[CH:6]=[CH:7][C:20]([N:18]([CH3:19])[CH3:17])=[N:3][CH:4]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 885792-Pyridinamine, 5-iodo-

Produkt 1

HCID 234385795-Iodo-N,N-dimethylpyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-iodopyridine (1.00 g; 4.55 mmol) in 10 mL of DMF was added 545 mg of 60% NaH (13.6 mmol) and 0.85 mL of iodomethane (13.6 mmol). The mixture was stirred for 14 h, and the mixture was neutralized with 1M HOAc. The mixture was extracted with Et2O, the extract was washed with water and brine, dried with MgSO4, filtered, and concentrated. Chromatography (0–25% EtOAc in hexanes) provided 700 mg (2.82 mmol) of (5-iodo-pyridin-2-yl)-dimethyl-amine.

Aufarbeitung

  1. extractionThe mixture was extracted with Et2O
  2. washthe extract was washed with water and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-64ae3c3da26a426cbf3cfab7df1e8a7f
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214802B2

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