HCID 21186731, compound → HCID 21186684, compound

HRID 1384290Notes

Reaction equation

HRID 1384290 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:6]2=[N:7][C:8]=1[CH3:9]>C(Cl)Cl.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH3:9][C:8]1[N:7]=[C:6]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:5]2=[CH:4][C:3]=1[CH:2]=[O:1]

Participants

5

Reactant 1

HCID 21186731HCID 21186731, compound

Product 1

HCID 21186684HCID 21186684, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an atmosphere of argon, 3-hydroxymethyl-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (5.24 g, 27.4 mmol) was dissolved in methylene chloride (150.0 ml), and the solution was mixed with manganese dioxide (15.88 g, 137.0 mmol) at room temperature and stirred at the same temperature for 4 hours. The reaction solution was diluted with ethyl acetate and then filtered. The solvent in the resulting filtrate was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain the title compound (3.76 g, 74.0%) as white powder.

Workup

  1. filtrationfiltered
  2. customThe solvent in the resulting filtrate was evaporated under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-17db0659d7a94cf8a30611b382443ffc
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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