Aluminum(III) Chloride → HCID 14373280, compound

HRID 1756531Notes

Reaction equation

HRID 1756531 reaction equation
[N:1]1([CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:23])[CH:15]=[CH:16]C3C=CC=CC=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[N:1]1([CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[NH:13][C:14](=[O:23])[CH:15]=[CH:16]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 54413582HCID 54413582, compound

Product 1

HCID 14373280HCID 14373280, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 10.5 parts of N-[4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]-3-phenyl-2-propenamide in 110 parts of chlorobenzene were added 18.5 parts of aluminium chloride. The reaction mixture was stirred for 3 hours at 120° C. After cooling to room temperature, the product was extracted with ethyl acetate. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and methanol. The product was filtered off and dried, yielding 1.3 parts (15.4%) of 6-[(1H-imidazol-1-yl)phenylmethyl]-2(1H)-quinolinone; mp. 226.9° C. (compound 2).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe product was extracted with ethyl acetate
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (90:10 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanone and methanol
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-e74a048a17d94f5b8345b99117c347cf
Source dataset
uspto-grants-1995_08
Patent number
US05441954

Reaction notes

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