HCID 86736573, compound → HCID 178475111, compound

HRID 971396Notes

Reaction equation

HRID 971396 reaction equation
[CH2:1]([O:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]([N+:19]([O-])=O)[CH:10]=[C:11]([C:13](=[O:18])[NH:14][O:15][CH2:16][CH3:17])[CH:12]=1)=[O:6])[CH3:2].[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28]([OH:35])=[C:29]([C:32](=O)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]>[Pd].C(O)C>[C:22]([C:25]1[C:26](=[O:36])[O:27][C:28](=[O:35])[C:29](=[C:32]([NH:19][C:9]2[CH:10]=[C:11]([C:13](=[O:18])[NH:14][O:15][CH2:16][CH3:17])[CH:12]=[C:7]([C:5](=[O:6])[NH:4][O:3][CH2:1][CH3:2])[CH:8]=2)[CH3:33])[C:30]=1[OH:31])(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 86736573HCID 86736573, compoundHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178475111HCID 178475111, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.0 g. (0.0067 mol) of 3,5-bis-ethoxycarbamoylnitrobenzene in 150 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 colorless filtrate was added 1.42 g. (0.0064 mol) of 3,5-diacetyl-4,6-dihydroxy-2H-pyranone. The mixture was heated under reflux for 45 minutes, cooled and the product filtered to yield 5-acetyl-4-hydroxy-3-[1-(3,5-bis-ethoxycarbamoylphenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 234°-235° C.

Workup

  1. filtrationthe catalyst was filtered
  2. additionto the colorless filtrate was added 1.42 g
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 45 minutes
  5. temperaturecooled
  6. filtrationthe product filtered

Sources & evidence

ORD record
ord-d72ea0a2d7234832b9734be205ed2143
Source dataset
uspto-grants-1979_07
Patent number
US04160021

Reaction notes

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