4-Fluoroaniline → HCID 178467269, compound

HRID 437967Notes

Reaction equation

HRID 437967 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[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:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[CH3:20])[C:17]=1[OH:18])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178467269HCID 178467269, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Fluoroaniline (2.2 g., 0.02 m.) is added to a hot solution of 4.24 g. (0.02 m.) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one in 150 ml. of methanol. The mixture is refluxed overnight and filtered to give 5-acetyl-3-[1-(p-fluorophenylamino)ethylidene]-4-hydroxy-2H-pyran-2,6-(3H)-dione, m.p. 199°-201° C.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. filtrationfiltered

Sources & evidence

ORD record
ord-52b2f877bc434bd0aab428aca5213309
Source dataset
uspto-grants-1977_06
Patent number
US04032652

Reaction notes

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