Potassium Carbonate → HCID 59145913, compound

HRID 887773Notes

Reaction equation

HRID 887773 reaction equation
[CH:1]1[C:6]2[CH:7]([CH2:10][C:11]#[N:12])[CH2:8][CH2:9][C:5]=2[CH:4]=[CH:3][N:2]=1.[NH2:13]OC1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O.[C:27]([O:33][CH2:34][CH3:35])(=[O:32])[C:28]#[C:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[C:11]([CH2:10][CH:7]1[C:6]2[C:1]3[N:2]([N:13]=[C:29]([CH2:30][CH3:31])[C:28]=3[C:27]([O:33][CH2:34][CH3:35])=[O:32])[CH:3]=[CH:4][C:5]=2[CH2:9][CH2:8]1)#[N:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 99169Ethyl pent-2-yn-1-oateHCID 591458942-(6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)acetonitrile

Product 1

HCID 59145913HCID 59145913, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6,7-dihydro-5H-cyclopenta[c]pyridin-7-ylacetonitrile (1.77 g, 11.2 mmol) in acetonitrile (22 mL) was added 1-(aminooxy)-2,4-dinitrobenzene (5.00 g, 25.1 mmol), and the mixture was stirred at 40° C. for 16 hr. The solvent was evaporated under reduced pressure. Half of the residue was dissolved in dimethylformamide (22 mL), ethyl 2-pentynoate (886 μL, 6.72 mmol) and potassium carbonate (1.55 g, 11.2 mmol) were added, and the mixture was stirred at room temperature for 16 hr. The reaction solution was diluted with water, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60) to give the title compound (644 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionHalf of the residue was dissolved in dimethylformamide (22 mL)
  3. stirringthe mixture was stirred at room temperature for 16 hr
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60)

Sources & evidence

ORD record
ord-79e03ac42bc047589ba008e97d52a013
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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