1,3-Diphenyl-2-propanone → 3,5-diphenyl-4(1H)-pyridone

HRID 261771

Reaction equation

HRID 261771 reaction equation
[Na][Na].O[CH:4]=[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6](=[O:16])[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:8]O.C1(CC(=O)CC2C=CC=CC=2)C=CC=CC=1.C(OCC)=O.C[O-].[Na+].CC(=O)C=C=C.C1(C2C(=O)C(C3C=CC=CC=3)=COC=2)C=CC=CC=1.O1C=CC=CC1=O.C([O-])(=O)C.[NH4+:83]>>[C:17]1([C:5]2[C:6](=[O:16])[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][NH:83][CH:4]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

10

Reactant 9

HCID 75931,3-Diphenyl-2-propanoneHCID 8025Ethyl formateHCID 681542H-Pyran-2-oneHCID 141233DisodiumHCID 2821893,5-diphenyl-4H-pyran-4-oneHCID 517165Ammonium AcetateHCID 109313673,4-Pentadien-2-oneHCID 10942334Sodium MethoxideHCID 705837841,5-Dihydroxy-2,4-diphenyl-1,4-pentadien-3-one

Product 1

HCID 124666803,5-diphenyl-4(1H)-pyridone

Procedure

The compounds of this invention can be prepared by various synthetic routes. Benary and Bitter, Ber. 61, 1058 (1928) taught the synthesis of an intermediate disodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one by the condensation of 1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium methoxide. The intermediate pentadienone is neutralized by strong acid and forms 3,5-diphenyl-4-pyrone. Reaction of the pyrone with ammonium acetate at an elevated temperature produces 3,5-diphenyl-4(1H)-pyridone.

Workup

  1. customThe compounds of this invention can be prepared by various synthetic routes

Sources & evidence

ORD record
ord-4b6acbf9a2b94c81a270b9f9ecf40673
Source dataset
uspto-grants-1979_05
Patent number
US04152136

Linked notes

Loading…