Flavanone → 3(3-Acetylaminobenzylidene)-flavanone

HRID 476606

Reaction equation

HRID 476606 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[CH2:3][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)(=[O:20])[CH3:19]>N1CCCCC1.C(Cl)(Cl)Cl>[C:18]([NH:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[C:3]1[C:4](=[O:5])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:1][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 10251FlavanoneHCID 256849N-(3-formylphenyl)acetamide

Product 1

HCID 544909013(3-Acetylaminobenzylidene)-flavanone

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6212ChloroformSolvent

Procedure

A solid mixture of 9 g flavanone, 7.2 g 3-acetylaminobenzaldehyde and 5 drops piperidine is heated at 150°-160° C. for 3 hours. After allowing to cool, the crude brown glass is dissolved in chloroform and eluted from silicagel with chloroform. The pale yellow oil, obtained on evaporation of the solvent is crystallized from hexane and ethyl acetate to give 3(3-acetylaminobenzylidene)-flavanone as a cream coloured solid; m.p. 172°-173° C.

Workup

  1. temperatureis heated at 150°-160° C. for 3 hours
  2. temperatureto cool
  3. washeluted from silicagel with chloroform
  4. customThe pale yellow oil, obtained on evaporation of the solvent
  5. customis crystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-a9263f90fdaa436fa0e4abe4c0c2c154
Source dataset
uspto-grants-1989_12
Patent number
US04885298

Linked notes

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