Ammonia → 5-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

HRID 2233338Notes

Reaction equation

HRID 2233338 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)C(O)=COC=1CO.COC1C(OC(C(O)C2C=CC(O)=C(OC)C=2)CO)=CC=CC=1.[NH3:51]>C(O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[NH:51][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3840Kojic AcidHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 6424189Guaiacylglycerol-beta-guaiacyl ether

Product 1

HCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one (9.7 g, 42 mmole; prepared from Kojic acid by the method of Erol, D. J. Med. Chem. 1994, 29, 893) concentrated aqueous ammonia (100 mL), and ethanol (20 mL) was heated at reflux overnight. The mixture was allowed to cool to RT and the solid was collected, washed with Et2O and dried in vacuo to afford the title compound (5.9 g, 61%): MS (APCI+) m/e 232 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customthe solid was collected
  3. washwashed with Et2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3f381d80707d4fe0a8675e1777d212ec
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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