HCID 57815289, compound → HCID 57815260, compound

HRID 385527Notes

Reaction equation

HRID 385527 reaction equation
[O:1]1[C:11]2[CH:10]=[C:9]([CH2:12][OH:13])[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:1]1[C:11]2[CH:10]=[C:9]([CH:12]=[O:13])[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57815289HCID 57815289, compound

Product 1

HCID 57815260HCID 57815260, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

To a solution of 13 g of (3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-yl)methanol in 250 mL of chloroform, 13 g of manganese dioxide was added, and the mixture was stirred at room temperature for 30 minutes. Thereto was further added 20 g of manganese dioxide dividedly, the mixture was then stirred at room temperature for 20 minutes and at 60 to 70° C. for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, the insoluble substance was then filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=1:1 to obtain 2.2 g of 3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridine-8-carbaldehyde as a light yellowish white solid.

Workup

  1. stirringthe mixture was then stirred at room temperature for 20 minutes and at 60 to 70° C. for 1 hour 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe insoluble substance was then filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b8038c1f7ec949708c01eec7f6b655d3
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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