4-Acetamidobenzaldehyde → HCID 76168093, compound

HRID 597717Notes

Reaction equation

HRID 597717 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:3])[CH3:2].[C:16]([NH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)(=[O:18])[CH3:17]>N1CCCCC1.C(Cl)(Cl)Cl>[C:16]([NH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:2][C:1]([CH:4]2[C:9]([OH:10])=[C:8]([C:11](=[O:13])[CH3:12])[C:7](=[O:14])[O:6][C:5]2=[O:15])=[O:3])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 739424-AcetamidobenzaldehydeHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 76168093HCID 76168093, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6212ChloroformSolvent

Procedure

To a mixture of 2.11 g. (0.01 m.) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one and 1.63 g. (0.01 m.) of p-acetamidobenzaldehyde in 200 ml. of chloroform is added with stirring 25 drops of piperidine. The resulting solution is refluxed and azeotroped for 12 hours, filtered hot and the solid is washed with dilute hydrochloric acid, water and ether to give 3-(p-acetamidocinnamoyl)-5-acetyl-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 230°-231° C.

Workup

  1. additionTo a mixture of 2.11 g
  2. temperatureThe resulting solution is refluxed
  3. customazeotroped for 12 hours
  4. filtrationfiltered hot
  5. washthe solid is washed with dilute hydrochloric acid, water and ether

Sources & evidence

ORD record
ord-829926e6c8d6418298d7c5a7eb04d643
Source dataset
uspto-grants-1977_03
Patent number
US04015009

Reaction notes

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