تفاعل #70733

معادلة التفاعل

4,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

sodium acetate

HCl

→

pure compound

3-(Aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىdry Parr bottle
2. 2
   workup.ADDITIONa small amount of acetic acid was added
3. 3
   أخرىThe bottle was capped
4. 4
   ترشيحThe reaction mixture was filtered
5. 5
   أخرىThe solvent was removed
6. 6
   أخرىto give a residue, which
7. 7
   ترشيحthe formed solids were filtered
8. 8
   تركيزThe yellow filtrate was concentrated
9. 9
   workup.ADDITIONTo the crude compound was added 30 mL of conc. HCl and 150 mL EtOH
10. 10
    workup.STIRRINGstirred at 0° C. for 2 h
11. 11
    ترشيحThe formed solids were filtered
12. 12
    غسيلwashed with cold EtOH, ether
13. 13
    أخرىdried
14. 14
    أخرىThe product was collected as 36 g
15. 15
    أخرىprepared on smaller scales
16. 16
    أخرىtriturated with ether

الإجراء التجريبي

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).

المصدر