Sodium periodate → HCID 86027543, compound

HRID 633839Notes

Reaction equation

HRID 633839 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][CH:19]([OH:22])CO)=[CH:15][C:14]([O:23][CH3:24])=[CH:13][CH:12]=2>O.CC(C)=O>[Cl:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][CH:19]=[O:22])=[CH:15][C:14]([O:23][CH3:24])=[CH:13][CH:12]=2

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 69218622HCID 69218622, compound

Product 1

HCID 86027543HCID 86027543, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium periodate (2.88 g, 13.5 mmol, 1.2 eq) in water (30 mL) is added dropwise at 0° C. to a stirred solution of 3-(3-chloro-6-methoxy-quinolin-4-yl)-propane-1,2-diol (3.0 g, 11.2 mmol, 1.0 eq) in acetone (50 mL) and water (20 mL). After 30 minutes stirring at 0° C. the reaction mixture is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to afford (3-chloro-6-methoxy-quinolin-4-yl)-acetaldehyde as a light brown solid (2.6 g, 99% yield).

Workup

  1. extractionis extracted with ethyl acetate (3×100 mL) and water (100 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac6be54880454d1fb1352e91e204210f
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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