1,4-Dioxane → (2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

HRID 627506Notes

Reaction equation

HRID 627506 reaction equation
O1CCOCC1.[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)[OH:26])[CH:14]=2)[N:9]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)=[O:26])[CH:14]=2)[N:9]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 86716079(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol

Product 1

HCID 86716078(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

1,4-dioxane (7.5 mL) and manganese (IV) dioxide (447 mg, 5.14 mmol) were added to crude (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol (Intermediate 37, step a, 1.03 mmol assuming theoretical yield in prior step). The resulting black suspension was heated in a 100° C. oil bath in a sealed tube for 3 hours. The mixture was allowed to cool, was diluted with DCM, and was filtered through Celite®. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane) to afford slightly impure title compound which was used without further purification.

Workup

  1. customassuming theoretical yield in prior step)
  2. temperatureto cool
  3. filtrationwas filtered through Celite®
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane)

Sources & evidence

ORD record
ord-64f36882e8904d14aa75d2c3cb5cb98a
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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