2-Chloroaniline → HCID 178467262, compound

HRID 437964Notes

Reaction equation

HRID 437964 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([C:12]1[C:13](=[O:23])[O:14][C:15]([OH:22])=[C:16]([C:19](=O)[CH3:20])[C:17]=1[OH:18])(=[O:11])[CH3:10]>CO>[C:9]([C:12]1[C:13](=[O:23])[O:14][C:15](=[O:22])[C:16](=[C:19]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[Cl:1])[CH3:20])[C:17]=1[OH:18])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178467262HCID 178467262, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

o-Chloroaniline (2.55 g., 0.02 m.) is added to 4.24 g. (0.02 m.) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one in 150 ml. of methanol and the mixture is refluxed overnight. The reaction mixture is concentrated, cooled and filtered to give 5-acetyl-3-[1-(o-chlorophenylamino)ethylidene]-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 143°-145° C.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9cde278dbf644e908d76a66960ba9c0e
Source dataset
uspto-grants-1977_06
Patent number
US04032652

Reaction notes

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