Ammonium Acetate → HCID 20443937, compound

HRID 355007Notes

Reaction equation

HRID 355007 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=O.[C:18]([O-])(=O)[CH3:19].[NH4+:22]>CO>[CH3:11][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[CH:19]=[C:14]([C:15]([OH:17])=[O:16])[CH:13]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[N:22]=2)=[CH:10][CH:1]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 5153185HCID 5153185, compound

Product 1

HCID 20443937HCID 20443937, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.92 g (0.01 mole) of the appropriate pyridinium salt, 2.26 g (0.01 mole) of β-(2-naphthoyl)acrylic acid and 8.5 g of ammonium acetate in 20 ml of methanol is heated at reflux for 6 hr. The mixture is concentrated and the residue is diluted with water and extracted with methylene chloride. The organic layer is concentrated and the residue is chromatographed on silica gel using 5% methanol-1% acetic acid-94% methylene chloride. The product is recrystallized from ethanol yielding 1.14 g (33.6%) of the titled crystals with a melting point of 272°-274° C. The C:H:N ratio is 81.32:5.01:4.16.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hr
  3. concentrationThe mixture is concentrated
  4. additionthe residue is diluted with water
  5. extractionextracted with methylene chloride
  6. concentrationThe organic layer is concentrated
  7. customthe residue is chromatographed on silica gel using 5% methanol-1% acetic acid-94% methylene chloride
  8. customThe product is recrystallized from ethanol yielding 1.14 g (33.6%) of the titled crystals with a melting point of 272°-274° C

Sources & evidence

ORD record
ord-cef9bf9ec08246df80ccd3aeb73d25b8
Source dataset
uspto-grants-1983_03
Patent number
US04377586

Reaction notes

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