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 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).

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 pressur
9. customThe residue was dried in vacuo

ORDレコード

ord-5cf1b284c2ea442eb8e0cbc1d7e3904f

出典データセット

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05599816