Chlorobenzene → HCID 23369598, compound

HRID 1900707Notes

Reaction equation

HRID 1900707 reaction equation
ClC1C=CC=CC=1.C([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:28])=[C:15]([NH:17][C:18](=[O:27])[CH:19]=[CH:20]C2C=CC=CC=2)[CH:16]=1)C.[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCC>[OH:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:28])=[C:15]2[C:16]=1[CH:20]=[CH:19][C:18](=[O:27])[NH:17]2

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 53733602HCID 53733602, compound

Product 1

HCID 23369598HCID 23369598, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Chlorobenzene (28.6 ml) was added to N-(5-ethoxy-2-methylphenyl)cinnamamide (3.9 g, 14.8 mmol). While stirring the mixture in a hot bath (125° C.), aluminum chloride (9.2 g, 69.0 mmol) was added to the mixture, followed by stirring for 30 minutes. After the mixture was cooled, it was poured into ice-water, to which n-hexane was added. Precipitated crystals were collected. The crystals were dissolved in chloroform-methanol (4:1). The solution was dried and condensed. The resultant residue was washed with chloroform, then dissolved in chloroform-methanol (4:1) again. The solution was condensed again. The residue was washed with chloroform and then dissolved in methanol. The resultant solution was treated with activated carbon. 2.4 g of 5-hydroxy-8-methylcarbostyril was obtained as colorless crystals (92.7%).

Workup

  1. additionwas added to the mixture
  2. temperatureAfter the mixture was cooled
  3. additionwas added
  4. customPrecipitated crystals
  5. customwere collected
  6. dissolutionThe crystals were dissolved in chloroform-methanol (4:1)
  7. customThe solution was dried
  8. customcondensed
  9. washThe resultant residue was washed with chloroform
  10. dissolutiondissolved in chloroform-methanol (4:1) again
  11. customcondensed again
  12. washThe residue was washed with chloroform
  13. dissolutiondissolved in methanol
  14. additionThe resultant solution was treated with activated carbon

Sources & evidence

ORD record
ord-2d5d83c2386d4632afa4ee7c1ae86fbd
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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