(4-Ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol → 4-Ethoxy-3-methanesulfonyl-quinoline-6-carbaldehyde

HRID 1297736Notes

Reaction equation

HRID 1297736 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=2)[N:7]=[CH:6][C:5]=1[S:16]([CH3:19])(=[O:18])=[O:17])[CH3:2]>ClCCl.[O-2].[Mn+2]>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[O:15])[CH:12]=2)[N:7]=[CH:6][C:5]=1[S:16]([CH3:19])(=[O:18])=[O:17])[CH3:2]

Participants

4

Reactant 1

HCID 58585781(4-Ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol

Product 1

HCID 585857684-Ethoxy-3-methanesulfonyl-quinoline-6-carbaldehydeYield 55%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol (example 74b, 25.4 m mol) in anhydrous dichloromethane (500 mL), manganese oxide (13.3 g, 152.4 mmol) was added. The reaction mixture was stirred at 25 degrees for 6 hours. After the reaction, the solid was filtered out; the filtrate was concentrated in vacuo. Column chromatography gave 4-ethoxy-3-methanesulfonyl-quinoline-6-carbaldehyde (3.92 g, 55%). LC-MS m/e 280 (MH+).

Workup

  1. customAfter the reaction
  2. filtrationthe solid was filtered out
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ba39eec250494fbe92f840cb9261f42e
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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