2-(Azidomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone → 4(1H)-Pyridinone, 2-(aminomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-

HRID 1252605Notes

Reaction equation

HRID 1252605 reaction equation
[N:1]([CH2:4][C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1)=[N+]=[N-]>CO>[NH2:1][CH2:4][C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1

Participants

3

Reactant 1

HCID 141824732-(Azidomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

Product 1

HCID 120385614(1H)-Pyridinone, 2-(aminomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-Yield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Azidomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone (1.0 g, 2.89 mmol) was dissolved in 50 ml of methanol and 0.10 g of platinic oxide was added. Hydrogen was bubbled through the mixture for 30 minutes and the catalyst filtered off by suction over Hyflo. The filtrate was evaporated in vacuo and the oily residue triturated with ether to afford crystalline title compound (0.89 g), melting point 207° C.

Workup

  1. customHydrogen was bubbled through the mixture for 30 minutes
  2. filtrationthe catalyst filtered off by suction over Hyflo
  3. customThe filtrate was evaporated in vacuo
  4. customthe oily residue triturated with ether

Sources & evidence

ORD record
ord-f1d531c1fcab42c4806a19004a5a001d
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

Loading…