Water → HCID 21186679, compound

HRID 1384287Notes

Reaction equation

HRID 1384287 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].S(=O)(=O)(O)[OH:19].O.[Cr](O)(O)(=O)=O>C(O)(=O)C.CC(O)C>[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:19])[C:5]2=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 21186750HCID 21186750, compound

Product 1

HCID 21186679HCID 21186679, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3776IsopropanolSolvent

Procedure

Ethyl methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (2.50 g, 10.1 mmol) was dissolved in acetic acid (7.0 ml), the solution was mixed with concentrated sulfuric acid (1.4 ml), and then 11% acetic acid aqueous solution (4.8 ml) of chromic anhydride (1.41 g, 14.1 mmol) was added thereto at 10 to 15° C. spending about 1 hour. After 6 hours of stirring at room temperature, water was added to the reaction solution to which was subsequently added dropwise 2-propanol at 0° C. to decompose excess chromic acid. The solvent was evaporated under reduced pressure, the thus obtained residue was neutralized with 20% sodium hydroxide aqueous solution at 0° C. and mixed with chloroform, and then the insoluble matter was removed by celite filtration and washed with chloroform. The resulting filtrate was extracted with chloroform, washed with water and saturated brine in that order and then 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 (284.7 mg, 10.8%) as colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customwas neutralized with 20% sodium hydroxide aqueous solution at 0° C.
  3. additionmixed with chloroform
  4. customthe insoluble matter was removed by celite filtration
  5. washwashed with chloroform
  6. extractionThe resulting filtrate was extracted with chloroform
  7. washwashed 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-b90422faef134edb8b693282451dadfa
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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