4-Acetamidobenzaldehyde → HCID 76168093, compound

HRID 1764742Notes

Reaction equation

HRID 1764742 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-2524c61721a748b0a4fa333d17b90d6a
Source dataset
uspto-grants-1978_09
Patent number
US04117226

Reaction notes

Loading…