Selenium Dioxide → HCID 86707455, compound

HRID 338927Notes

Reaction equation

HRID 338927 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2)[CH3:5].[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH:17]=[O:19])[CH:13]=[CH:12]2)[CH3:5]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 70982964HCID 70982964, compound

Product 1

HCID 86707455HCID 86707455, compoundYield 82.5%

Reagents, catalysts & solvents 1

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

Procedure

To 8-(1-methoxypropan-2-yloxy)-2-methylquinoline (1.0 g, 4.32 mmol) in dioxane/water (10/1 mL) was added selenium dioxide (0.576 g, 5.19 mmol) and the reaction was heated to reflux for 2 hours. The reaction was concentrated to dryness and the residue purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde (874 mg, 82.4% yield) as a solid

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated to dryness
  4. customthe residue purified by reverse phase chromatography (SP4, 25M
  5. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-b6adbdec33b74981894f652adae764ac
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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