Sodium Carbonate → 6,7-Dihydro-7-oxo-5H-cyclopenta[b]pyridine-3-carbonitrile

HRID 1626126Notes

Reaction equation

HRID 1626126 reaction equation
[OH:1][CH:2]1[C:10]2[N:9]=[CH:8][C:7]([C:11]#[N:12])=[CH:6][C:5]=2[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[O:1]=[C:2]1[C:10]2[N:9]=[CH:8][C:7]([C:11]#[N:12])=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 159087TriacetoxyperiodinaneHCID 68227161HCID 68227161, compound

Product 1

HCID 682273326,7-Dihydro-7-oxo-5H-cyclopenta[b]pyridine-3-carbonitrileYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 7-hydroxy-6,7-dihydro-5H-[1]pyrindine-3-carbonitrile (1.05 g, 6.56 mmol) in dichloromethane (50 ml) at 0° C. was added Dess-Martin periodinane (2.92 g, 6.88 mmol) and the mixture was stirred at 23° C. for 2 hours. Poured on a solution of sodium carbonate (1M) and extracted twice with dichloromethane. The organic layers were washed with a diluted solution of sodium hydrogensulfite and brine, dried over sodium sulphate, filtered and evaporated to give a grey solid. The residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 7-oxo-6,7-dihydro-5H-[1]pyrindine-3-carbonitrile (855 mg, 78%) as a dark green solid. MS (ISP): m/z=159.1 [M+H]+.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe organic layers were washed with a diluted solution of sodium hydrogensulfite and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a grey solid
  7. customThe residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-e1e267b28dfb43779d35784df8d6e87d
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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