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

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 3×50 mL of methylene chloride. The organic combined extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 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).

1. customthe tube was sealed
2. customthe solvent was removed under reduced pressure
3. additionTo the residue was added 50 mL of 10% aqueous sodium carbonate solution
4. extractionthe resultant aqueous mixture was extracted with 3×50 mL of methylene chloride
5. extractionThe organic combined extract
6. dry with materialwas dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was dried in vacuo

ORD-Eintrag

ord-fdcb564008cf477d9ba0b62666e717fe

Quelldatensatz

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05580872