Dichloromethane → 7-Ethoxy-6-fluoroquinoline-2-carbaldehyde

HRID 338946Notes

Reaction equation

HRID 338946 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH3:14])=[N:11]2)=[CH:6][C:5]=1[F:15])[CH3:2].[Se](=O)=[O:17].C(Cl)Cl.[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH:14]=[O:17])=[N:11]2)=[CH:6][C:5]=1[F:15])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24007Selenium DioxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 709832187-Ethoxy-6-fluoro-2-methylquinoline

Product 1

HCID 867074687-Ethoxy-6-fluoroquinoline-2-carbaldehyde

Reagents, catalysts & solvents 1

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

Procedure

To 7-ethoxy-6-fluoro-2-methylquinoline (180 mg, 0.877 mmol) in dioxane/water (5 mL/0.05 mL) was added selenium dioxide (136 mg, 1.23 mmol) and the reaction was heated to reflux for 2 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 2 hours
  3. temperatureAfter cooling
  4. concentrationAfter concentration
  5. customthe residue was used in the next step without purification

Sources & evidence

ORD record
ord-e7587684c5c246f185246021301eaa2d
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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