Hydrochloric Acid → 3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochloride

Temperature

0 °C

Palladium on carbon (10%) (3.24 g) was charged into a 2 L dry Parr bottle and a small amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (30 g, 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol), platinum oxide (0.218 g), and acetic acid (1 L). The bottle was capped, placed on Parr apparatus, and shaken under an atmosphere of H2 (100 psi) for 2 days. The reaction mixture was filtered. The solvent was removed to give a residue, which was treated with 150 mL of conc. HCl, and the formed solids were filtered. The yellow filtrate was concentrated. To the crude compound was added 30 mL of conc. HCl and 150 mL EtOH, the contents cooled to 0° C., and stirred at 0° C. for 2 h. The formed solids were filtered, washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batch was combined with other batches prepared on smaller scales and triturated with ether to give 51 g of pure compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (br s, 1H) 8.13 (br s, 3H) 5.93-6.01 (m, 1H) 3.72-3.80 (m, 2H) 2.22 (s, 3H) 2.16 (s, 3H).

1. customdry Parr bottle
2. additiona small amount of acetic acid was added
3. customThe bottle was capped
4. filtrationThe reaction mixture was filtered
5. customThe solvent was removed
6. customto give a residue, which
7. filtrationthe formed solids were filtered
8. concentrationThe yellow filtrate was concentrated
9. additionTo the crude compound was added 30 mL of conc. HCl and 150 mL EtOH
10. stirringstirred at 0° C. for 2 h
11. filtrationThe formed solids were filtered
12. washwashed with cold EtOH, ether
13. customdried
14. customThe product was collected as 36 g
15. customprepared on smaller scales
16. customtriturated with ether

ORD record

ord-0bdb249af5da436cb308149a28cee969

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536179B2