HCID 70224223, compound → HCID 21186674, compound

HRID 1384265Notes

Reaction equation

HRID 1384265 reaction equation
[CH3:1][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]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(OC(=O)C)(=O)C>[C:14]([O:16][CH:9]1[C:6]2=[N:7][C:2]([CH3:1])=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[C:5]2[CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:15])[CH3:3]

Participants

3

Reactant 1

HCID 70224223HCID 70224223, compound

Product 1

HCID 21186674HCID 21186674, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (1.00 g, 4.02 mmol) was dissolved in acetic anhydride (7.0 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 saturated sodium bicarbonate 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 resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain the title compound (482.5 mg, 45.8%) as pale brown oil.

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 saturated sodium bicarbonate 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. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1)

Sources & evidence

ORD record
ord-c4dc63af7d0241969ffa3a49b100cff4
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…