Potassium Carbonate → HCID 21186702, compound

HRID 1384275Notes

Reaction equation

HRID 1384275 reaction equation
C([O:4][CH:5]1[C:10]2=[N:11][C:12]([CH3:20])=[C:13]([C:15]([O:17][CH2:18]C)=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][CH:5]1[C:10]2=[N:11][C:12]([CH3:20])=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21186734HCID 21186734, compound

Product 1

HCID 21186702HCID 21186702, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 8-acetoxy-2-methyl-5,6,7,8-tetrahydrocyclohexa[b]pyridine-3-carboxylate (6.12 g, 22.1 mmol) was dissolved in ethanol (30.0 ml), and the solution was mixed with potassium carbonate (3.68 g) and stirred at from 0° C. to room temperature for 14 hours. The solvent was evaporated under reduced pressure, and the thus obtained residue was mixed with water and ethyl acetate and extracted with ethyl acetate. The thus obtained 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 (4.59 g, 93.9%) as white amorphous.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe thus obtained residue was mixed with water and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1)

Sources & evidence

ORD record
ord-2864ffea15504c03b3a36881a4242abf
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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