Hydrochloric Acid → HCID 178474271, compound

HRID 2398764Notes

Reaction equation

HRID 2398764 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)(=[O:3])[CH3:2].Cl.Cl.C(NC1C=CC(O)=C(N)C=1)(=O)C.[C:29]([C:32]1[C:33](=[O:43])[O:34][C:35]([OH:42])=[C:36]([C:39](=O)[CH3:40])[C:37]=1[OH:38])(=[O:31])[CH3:30].C(=O)(O)[O-].[Na+]>O.[Pd].CO.C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH:12][C:39](=[C:36]2[C:37]([OH:38])=[C:32]([C:29](=[O:31])[CH3:30])[C:33](=[O:43])[O:34][C:35]2=[O:42])[CH3:40])[CH:6]=1)(=[O:3])[CH3:2]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3322389N-(4-Hydroxy-3-nitrophenyl)acetamideHCID 21434080HCID 21434080, compoundHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178474271HCID 178474271, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedures of Example 1, 4.0 g. (0.0204 mol) of 4-acetamido-2-nitrophenol (prepared by acetylation of the corresponding amine) is hydrogenated in a mixture of 150 ml. of ethanol, 3.3 ml. of concentrated hydrochloric acid and 0.5 g. of 10% palladium-on-carbon in a Parr apparatus at room temperature. Filtration of the reaction mixture gives a powder which is dissolved in a minimum amount of water and filtered. This aqueous solution of 4-acetamido-2-aminophenol hydrochloride is added to a mixture of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one (3.42 g., 0.0162 mol) and 1.36 g. (0.0162 mol) of sodium bicarbonate in 130 ml. of methanol. After 18 hours at reflux, the reaction mixture is filtered and the solid is recrystallized from dioxane-acetonitrile to give 3-[1-(5-acetamido-2-hydroxyphenylamino)ethylidene]-5-acetyl-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 253°-254° C. (dec.).

Workup

  1. additionis hydrogenated in a mixture of 150 ml
  2. customat room temperature
  3. filtrationFiltration of the reaction mixture
  4. customgives a powder which
  5. filtrationfiltered
  6. temperatureAfter 18 hours at reflux
  7. filtrationthe reaction mixture is filtered
  8. customthe solid is recrystallized from dioxane-acetonitrile

Sources & evidence

ORD record
ord-da41766049cf466b83cda1f24a33c683
Source dataset
uspto-grants-1977_05
Patent number
US04025642

Reaction notes

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