Reaktion #1962

Reaktionsgleichung

4-Chloro-5-fluoro-alpha-bromo-2-picoline

Methylamine

→

title compound

Ausbeute 70.0%

4-Chloro-5-fluoro-2-(N-methylaminomethyl)-pyridine

Ausbeute 70.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe tube was sealed
2. 2
   Sonstigethe solvent was removed under reduced pressure
3. 3
   workup.ADDITIONTo the residue was added 50 mL of 10% aqueous sodium carbonate solution
4. 4
   Extraktionthe resultant aqueous mixture was extracted with 3 X 50 mL of methylene chloride
5. 5
   ExtraktionThe organic combined extract
6. 6
   Trocknenwas dried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressur
9. 9
   SonstigeThe residue was dried in vacuo

Vorschrift

4-Chloro-5-fluoro-alpha-bromo-2-picoline (1.37 g, 6.1 mmol), from Step 1 was dissolved in 15 mL of methanol in a pressure tube. Methylamine (3 mL of 40% aqueous solution) was added to the tube and the tube was sealed. The reaction mixture was stirred at ambient temperature for 26 hours and then the solvent was removed under reduced pressure. To the residue was added 50 mL of 10% aqueous sodium carbonate solution and the resultant aqueous mixture was extracted with 3 X 50 mL of methylene chloride. The organic combined extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressur. The residue was dried in vacuo to give 754 mg g (70% yield) of the title compound; MS DCI-NH3M/Z: 175 (M+H)+ base; 1H NMR (CDCl3) d 2.50 (s, 3H), 3.90 (s, 2H), 7.47 (d, 1H), 8.42 (s, 1H).

Quelle