Potassium Carbonate → 4-(3-chlorophenyl)-6-(3-iodobenzoyl)-2(1H)-quinolinone

HRID 346984Notes

Reaction equation

HRID 346984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=4)=[O:19])[CH:16]=3)[N:11]=[C:10]([O:27]C)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>Cl.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:19])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=4)[CH:16]=3)[NH:11][C:10](=[O:27])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21082028[4-(3-Chlorophenyl)-2-methoxy-6-quinolinyl](3-iodophenyl)-methanone

Product 1

HCID 210820354-(3-chlorophenyl)-6-(3-iodobenzoyl)-2(1H)-quinolinoneYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of intermediate (73) (0.0304 mol) in HCl 3N (150 ml) and THF (70 ml) was stirred and refluxed overnight, brought to room temperature, poured out into ice water and basified with potassium carbonate. The precipitate was filtered, washed with 2-propanone and dried, yielding 13 g (88%) of 4-(3-chlorophenyl)-6-(3-iodobenzoyl)-2(1H)-quinolinone (intermediate 74).

Workup

  1. temperaturerefluxed overnight
  2. custombrought to room temperature
  3. filtrationThe precipitate was filtered
  4. washwashed with 2-propanone
  5. customdried

Sources & evidence

ORD record
ord-df125b2042124c39917f6eb35422eafd
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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