Ammonium Hydroxide → (+/-)-6-[(1H-imidazol-1-yl)phenylmethyl]-4-phenyl-2(1H)-quinolinone

HRID 1739833Notes

Reaction equation

HRID 1739833 reaction equation
N1([CH:6]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH:15]=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)C3C=CC=CC=3)=[CH:9][CH:8]=2)C=CN=C1.[Cl-].[Al+3].[Cl-].[Cl-].[NH4+:40].[OH-:41]>ClC1C=CC=CC=1>[N:40]1([CH:6]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[NH:13][C:14](=[O:41])[CH:15]=[C:16]3[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=[CH:10][N:13]=[CH:14]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 15484950(+/-)-N-[4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]-3,3-diphenyl-2-propenamide

Product 1

HCID 15484951(+/-)-6-[(1H-imidazol-1-yl)phenylmethyl]-4-phenyl-2(1H)-quinolinoneYield 16%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of intermediate (1-c) (22.85 g) and aluminium chloride (48 g) in chlorobenzene (200 ml) was heated at 95° C. overnight. The mixture was cooled, poured into ice water, basified with NH4OH and evaporated till dryness. The residue was taken up in DCM and ethanol. The residue was filtered and evaporated. The residue was taken up in DCM and stirred with HCl 3N overnight. The mixture was extracted, the aqueous layer was washed with ethyl acetate, basified with NH4OAc and then extracted with ethyl acetate and the organic layer was dried (MgSO4) and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 95/5/0.05) (35-70 μm). The pure fractions were collected and evaporated, yielding 2.13 g (16%) of (±)-6-[(1H-imidazol-1-yl)phenylmethyl]-4-phenyl-2(1H)-quinolinone; mp. 253.0° C. (comp. 1).

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated till dryness
  3. filtrationThe residue was filtered
  4. customevaporated
  5. extractionThe mixture was extracted
  6. washthe aqueous layer was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialthe organic layer was dried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 95/5/0.05) (35-70 μm)
  11. customThe pure fractions were collected
  12. customevaporated

Sources & evidence

ORD record
ord-38e0d60ae6c5412c9dd241e2a542c6d6
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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