(3-Methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol → 3-Methanesulfonyl-4-phenyl-quinoline-6-carbaldehyde

HRID 1297701Notes

Reaction equation

HRID 1297701 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH2:21][OH:22])=[CH:10][CH:9]=2)(=[O:4])=[O:3]>C(Cl)Cl.[O-2].[Mn+2]>[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH:21]=[O:22])=[CH:10][CH:9]=2)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 58585810(3-Methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol

Product 1

HCID 585858373-Methanesulfonyl-4-phenyl-quinoline-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of (3-methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol (example 61 h, 90 mg, 0.29 mmol) in methylene chloride (10 ml), activated manganese oxide (250 mg, 2.88 mmol) was added. The reaction mixture was heated at the refluxing temperature for 45 min. After cooling to the room temperature, the reaction mixture was filtered through a bed of celit with methylene chloride. The filtrate was collected and concentrated in vacuo to give 3-methanesulfonyl-4-phenyl-quinoline-6-carbaldehyde. LC-MS m/e 312 (MH+).

Workup

  1. temperatureThe reaction mixture was heated at the refluxing temperature for 45 min
  2. filtrationthe reaction mixture was filtered through a bed of celit with methylene chloride
  3. customThe filtrate was collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d643763998554f12bbfcd15d3b7b0cec
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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