Reaction #1962

Reaction equation

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

Methylamine

→

title compound

Yield 70.0%

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

Yield 70.0%

Solvents

methanol

Conditions

Workup

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

Procedure

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).

Source