Dichloromethane → 7-Methoxy-6-methylquinoline-2-carbaldehyde

HRID 338951Notes

Reaction equation

HRID 338951 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH3:13])=[N:10]2)=[CH:5][C:4]=1[CH3:14].[Se](=O)=[O:16].C(Cl)Cl.[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[O:16])=[N:10]2)=[CH:5][C:4]=1[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24007Selenium DioxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 867074717-Methoxy-2,6-dimethylquinoline

Product 1

HCID 867074727-Methoxy-6-methylquinoline-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 7-methoxy-2,6-dimethylquinoline (580 mg, 3.10 mmol) in dioxane/water (15/0.015 mL) was added selenium dioxide (447 mg, 4.03 mmol) and the reaction was heated to reflux for 5 hours. After cooling, DCM was added followed by MgSO4. After concentration, the residue was used in the next step without purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. concentrationAfter concentration
  5. customthe residue was used in the next step without purification

Sources & evidence

ORD record
ord-c7f90c8963af42e3a605b51aad392744
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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