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

HRID 1820671

Reaction equation

HRID 1820671 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); MS (APCI+) m/z 232 (MH+).

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-4a33affb45054d03a1ddac0a88762632
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Linked notes

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