Water → HCID 21186768, compound

HRID 1384274Notes

Reaction equation

HRID 1384274 reaction equation
C[C:2]1[N+:7]([O-])=[C:6]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:5]2=[CH:4][C:3]=1C(OCC)=O.C(=O)([O-])[O-:20].[K+].[K+].O.[C:26](OCC)(=[O:28])[CH3:27]>C(OC(=O)C)(=O)C.CO>[N:7]1[C:27]2[C:5]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:6]3[O:28][CH:26]=2)[CH2:4][C:3](=[O:20])[CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 70224223HCID 70224223, compound

Product 1

HCID 21186768HCID 21186768, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (8.00 g, 32.1 mmol) was dissolved in acetic anhydride (56.0 ml) and heated under reflux for 1.5 hours. After cooling, excess acetic anhydride was evaporated under reduced pressure, the thus obtained residue was mixed with ice water and 40% sodium hydroxide aqueous solution and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the thus obtained reaction product (10.27 g, 32.1 mmol) was dissolved in methanol (40.0 ml), mixed with potassium carbonate (4.88 g) and stirred at 0° C. for 30 minutes. The reaction solution was mixed with water and ethyl acetate, and the thus precipitated crystals were collected by filtration to obtain pale yellow powder of 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrido[3,2-c]furan-3-one (2.69 g, 41.3%) as a low polar component The resulting filtrate was extracted with ethyl acetate, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. By evaporating the solvent under reduced pressure, methyl 9-hydroxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (4.20 g, 55.7%) was obtained in the form of white amorphous as a high polar component.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customexcess acetic anhydride was evaporated under reduced pressure
  5. additionthe thus obtained residue was mixed with ice water and 40% sodium hydroxide aqueous solution
  6. extractionextracted with ethyl acetate
  7. washthe resulting organic layer was washed with water and saturated brine in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-bfe5e1a4bd3548e3b54a1ef118ab77c6
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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