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

HRID 403241Notes

Reaction equation

HRID 403241 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 78.4%

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 1 M Na2CO3-sol. and extracted twice with dichloromethane. The organic layers were washed with diluted NaHSO3 solution and brine, dried over Na2SO4, 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, 5.14 mmol, 78.3%) as a dark green solid. MS (ISP): m/z=159.1 [(M+H)+].

Workup

  1. extractionand extracted twice with dichloromethane
  2. washThe organic layers were washed with diluted NaHSO3 solution and brine
  3. dry with materialdried over Na2SO4
  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-bab698731056422e9db87c76751cf04c
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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