Sulfuric Acid → N-[2-(1,6-dihydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethyl]propanamide

HRID 2389938Notes

Reaction equation

HRID 2389938 reaction equation
[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[CH:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[C:8]3=2)[O:3][CH2:2]1.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1.C(=O)([O-])O.[Na+]>[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH:11]=[C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[C:8]3=2)[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 66601781N-[2-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethyl]propanamide

Product 1

HCID 59179415N-[2-(1,6-dihydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethyl]propanamideYield 16%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-[2-(1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylidene)ethyl]propanamide (612 mg, 2.37 mmol) in xylene (20 mL) was added sulfuric acid (693 μL, 12.9 mmol), and the mixture was heated under reflux for 22 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate) to give the title compound (97.0 mg, yield 16%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-335962c957164424817f4d5d3d3c19bc
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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