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

HRID 1271691

Reaction equation

HRID 1271691 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-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-benzyloxy-2-hydroxymethyl-4-pyrone (prepared from Kojic acid by the method of D. Erol, J. Med. Chem., 1994, 29, 893) (9.7 g, 40 mmol), concentrated aqueous (880) ammonia (100 ml), and ethanol (20 ml) was heated to reflux overnight. The mixture was allowed to cool to room temperature then filtered. The resultant solid was washed with ether and dried in vacuo (5.9 g).

Workup

  1. temperatureto reflux overnight
  2. filtrationthen filtered
  3. washThe resultant solid was washed with ether
  4. customdried in vacuo (5.9 g)

Sources & evidence

ORD record
ord-d2bdf43fb97f4e6c8d1b0712e6581bd3
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Linked notes

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