1,4-Dioxane → 7-(Oxetan-3-yl)quinoline-2-carbaldehyde

HRID 339078Notes

Reaction equation

HRID 339078 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]3[CH2:15][O:14][CH2:13]3)=[CH:7][CH:8]=2)[N:3]=1.[O:16]1CCOCC1>O>[O:14]1[CH2:13][CH:12]([C:6]2[CH:5]=[C:4]3[C:9]([CH:10]=[CH:11][C:2]([CH:1]=[O:16])=[N:3]3)=[CH:8][CH:7]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 867075512-Methyl-7-(oxetan-3-yl)quinoline

Product 1

HCID 867075527-(Oxetan-3-yl)quinoline-2-carbaldehydeYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-7-(oxetan-3-yl)quinoline (0.020 g, 0.100 mmol) was dissolved in dioxane (5 mL) and water (0.05 mL). The reaction was treated with SeO2 (0.013 g, 0.120 mmol) and the mixture was heated to reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure to give 7-(oxetan-3-yl)quinoline-2-carbaldehyde (0.020 g, 0.0938 mmol, 93.4% yield) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a3a255a5aaa4105b2c3fb296f73aa21
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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