HCID 13779362, compound → HCID 178475110, compound

HRID 971397Notes

Reaction equation

HRID 971397 reaction equation
[CH2:1]([O:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=1)=[O:6])[CH3:2].[C:16]([C:19]1[C:20](=[O:30])[O:21][C:22]([OH:29])=[C:23]([C:26](=O)[CH3:27])[C:24]=1[OH:25])(=[O:18])[CH3:17]>[Pd].C(O)C>[C:16]([C:19]1[C:20](=[O:30])[O:21][C:22](=[O:29])[C:23](=[C:26]([NH:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:5](=[O:6])[NH:4][O:3][CH2:1][CH3:2])[CH:8]=2)[CH3:27])[C:24]=1[OH:25])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 13779362HCID 13779362, compoundHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178475110HCID 178475110, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.0 g. (0.0095 mol) of 3-ethoxycarbamoylnitrobenzene in 100 ml. of 2B ethanol was hydrogenated over 200 mg. of 10% palladium-on-carbon at 50 psi. Reduction was complete in 1 hour, the catalyst was filtered and to the filtrate was added 1.71 g. (0.0095 mol) of 3,5-diacetyl-4,6-dihydroxy-2H-pyranone. The mixture was heated under reflux for 1.5 hours, cooled, and the product filtered to yield 5-acetyl-4-hydroxy-3-[1-(3-ethoxycarbamoylphenylamino)ethylidene]-2H-pyran-2,6-(3H)-dione, m.p. 162°-164° C.

Workup

  1. filtrationthe catalyst was filtered and to the filtrate
  2. additionwas added 1.71 g
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 1.5 hours
  5. temperaturecooled
  6. filtrationthe product filtered

Sources & evidence

ORD record
ord-6624f7d61ee5400d88c1505d0a6a3318
Source dataset
uspto-grants-1979_07
Patent number
US04160021

Reaction notes

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