HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Diphenyl-2-propanone → 3,5-diphenyl-4(1H)-pyridone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Diphenyl-2-propanone | HCID 7593 | — |
| Reactant | Ethyl formate | HCID 8025 | — |
| Reactant | 2H-Pyran-2-one | HCID 68154 | — |
| Reactant | Disodium | HCID 141233 | — |
| Reactant | 3,5-diphenyl-4H-pyran-4-one | HCID 282189 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | 3,4-Pentadien-2-one | HCID 10931367 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | 1,5-Dihydroxy-2,4-diphenyl-1,4-pentadien-3-one | HCID 70583784 | — |
| Product | 3,5-diphenyl-4(1H)-pyridone | HCID 12466680 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04152136 |
| Source dataset | uspto-grants-1979_05 |
| ORD ID | ord-4b6acbf9a2b94c81a270b9f9ecf40673 |
| Source note | uspto-grants-1979_05 |