(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol → (2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 526828Notes

Reaction equation

HRID 526828 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:19]([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1>O1CCOCC1.C(Cl)Cl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)=[O:20])[CH:8]=2)[N:3]=1

Participants

5

Reactant 1

HCID 118006175(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol

Product 1

HCID 118006377(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Manganese (IV) oxide (1.17 g, 13.4 mmol) was added to a solution of (2,4-dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol (1.03 g, 2.68 mmol, Intermediate 2: step a) in 1,4-dioxane (15 mL). The resulting black suspension was fitted with a reflux condenser and was refluxed for 3 hours. The reaction mixture was cooled to room temperature, diluted with DCM, and was filtered through Celite®, washing with DCM. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 1-3% MeOH-DCM, first column; 10-25% acetone-EtOAc, second column) to afford the title compound as a white solid.

Workup

  1. customThe resulting black suspension was fitted with a reflux condenser
  2. temperaturewas refluxed for 3 hours
  3. filtrationwas filtered through Celite®
  4. washwashing with DCM
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash column chromatography (silica gel, 1-3% MeOH-DCM, first column; 10-25% acetone-EtOAc, second column)

Sources & evidence

ORD record
ord-981adc5c175446d9b2fad7d25b722bca
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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