1,4-Dioxane → HCID 86707408, compound

HRID 338841Notes

Reaction equation

HRID 338841 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]3)[CH2:3][CH2:2]1.[O:17]1CCOCC1>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[C:13]([CH:16]=[O:17])[CH:12]=[CH:11]3)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70983259HCID 70983259, compound

Product 1

HCID 86707408HCID 86707408, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8-(cyclopropylmethoxy)-2-methylquinoline (3.00 g, 14.1 mmol) in dioxane (100 mL) and water (1.0 mL) was added SeO2 (1.87 g, 16.9 mmol). The reaction mixture was stirred at 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 and the residue was purified by flash chromatography on silica gel (1:4 hexane/DCM) to give 8-(cyclopropylmethoxy)quinoline-2-carbaldehyde (3.1 g, 97.0%) as a solid

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solid was removed by filtration
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel (1:4 hexane/DCM)

Sources & evidence

ORD record
ord-d18110f6998c478cbb261c002ce04569
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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