4-Chloroaniline → 3-acetyl-5-[1-(4-chloroanilino)ethylidene]-4-hydroxypyran-2,6-dione

HRID 328596Notes

Reaction equation

HRID 328596 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=O)[CH3:2].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[C:11]([C:8]1[C:7](=[O:14])[O:6][C:5](=[O:15])[C:4](=[C:1]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][CH:19]=2)[CH3:2])[C:9]=1[OH:10])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 1784672663-acetyl-5-[1-(4-chloroanilino)ethylidene]-4-hydroxypyran-2,6-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,5-Diacetyl-4,6-dihydroxy-2H-pyran-2-one (5.3 g.) is dissolved in 200 ml. of boiling toluene and an equimolar amount of p-chloroaniline is added. The mixture is refluxed for 12 hours, cooled and filtered to yield 5-acetyl-3-[1-(p-chlorophenylamino)ethylidene]-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 205° -206° C.

Workup

  1. temperatureThe mixture is refluxed for 12 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e72bf439b2f44287a04386b7b524b3c0
Source dataset
uspto-grants-1977_04
Patent number
US04017633

Reaction notes

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