Nitric Acid → HCID 70224229, compound

HRID 1384269Notes

Reaction equation

HRID 1384269 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[CH:8][C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>>[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[C:8]([N+:1]([O-:4])=[O:2])[C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 70224223HCID 70224223, compound

Product 1

HCID 70224229HCID 70224229, compoundYield 92.4%

Conditions

Temperature
90 °C

Procedure

Fuming nitric acid (27.0 ml) was added dropwise to ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (3.10 g, 12.4 mmol) at 0° C., and the mixture was stirred at 90° C. for 2 hours. After cooling, the reaction solution was poured into ice water, mixed with 2 N sodium hydroxide aqueous solution and extracted with chloroform, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1) to obtain the title compound (3.38 g, 92.4%) as pale yellow powder.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washthe thus obtained organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-e172ef55557049279b148bb2cd118a60
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…