Water → (6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde

HRID 494986Notes

Reaction equation

HRID 494986 reaction equation
[OH:1][CH:2](CO)[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[O:15][CH3:16].O.I([O-])(=O)(=O)=O.[Na+].[Cl-].[Na+]>CO.O1CCCC1>[CH3:16][O:15][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[CH2:3][CH:2]=[O:1])[NH:11][C:10](=[O:14])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 23667635Sodium periodateHCID 576827997-(2,3-Dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 86601606(6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehydeYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

110 mg of 7-(2,3-dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one was dissolved in 2 ml of methanol and 1 ml of tetrahydrofuran. Thereafter, 2 ml of water containing 0.16 g of sodium metaperiodate was added to the reaction solution while cooling on ice. The obtained mixture was stirred at room temperature for 30 minutes. A saturated sodium chloride aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 87 mg of (6-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde. This compound was directly used in the following reaction without further purification.

Workup

  1. temperaturewhile cooling on ice
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-01c7efeeae8a4f4784777ebd24295df3
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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