Water → HCID 57682826, compound

HRID 494979Notes

Reaction equation

HRID 494979 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:13][CH:14]([OH:17])CO)=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.O.I([O-])(=O)(=O)=O.[Na+].[Cl-].[Na+]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[C:4]([CH2:13][CH:14]=[O:17])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 23667635Sodium periodateHCID 57682930HCID 57682930, compound

Product 1

HCID 57682826HCID 57682826, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.81 g of 3-(6-methoxyquinolin-5-yl)propane-1,2-diol was dissolved in 24 ml of tetrahydrofuran and 8 ml of methanol. Then, 12 ml of water containing 1.49 g of sodium metaperiodate was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at room temperature for 45 minutes. Thereafter, 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 0.72 g of (6-methoxyquinolin-5-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-d069cde5ade341b6b5a871c3c7c8ef2c
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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