HCID 21186702, compound → HCID 21186786, compound

HRID 1384280Notes

Reaction equation

HRID 1384280 reaction equation
[OH:1][CH:2]1[C:7]2=[N:8][C:9]([CH3:16])=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=[C:6]2[CH2:5][CH2:4][CH2:3]1>ClCCl.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH3:16][C:9]1[N:8]=[C:7]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]2=[CH:11][C:10]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 1

HCID 21186702HCID 21186702, compound

Product 1

HCID 21186786HCID 21186786, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 8-hydroxy-2-methyl-5,6,7,8-tetrahydrocyclohexa[b]pyridine-3-carboxylate (3.95 g, 17.9 mmol) was dissolved in dichloromethane (80.0 ml), and the solution was mixed with activated manganese dioxide (23.29 g) and stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate and then purified by a short column chromatography (ethyl acetate) and recrystallization (ethyl acetate-ether) to obtain the title compound (975.1 mg, 24.9%) as pale yellow needle crystals.

Workup

  1. custompurified by a short column chromatography (ethyl acetate) and recrystallization (ethyl acetate-ether)

Sources & evidence

ORD record
ord-aef7df74abf54958a3609bd1bb5ca099
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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