Water → HCID 21186673, compound

HRID 1384273Notes

Reaction equation

HRID 1384273 reaction equation
C([O:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:21])=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O.C(OCC)(=O)C>C(O)C>[OH:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:21])=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21186674HCID 21186674, compound

Product 1

HCID 21186673HCID 21186673, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 9-acetoxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (4.90 g, 16.81 mmol) was dissolved in ethanol (30 ml), and the solution was mixed with potassium carbonate (3.29 g) and stirred at from 0° C. to room temperature for 24 hours. There action solution was mixed with water and ethyl acetate, and the thus precipitated crystals were filtered. 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, the title compound (3.31 g, 79.9%) was obtained as pale yellow amorphous.

Workup

  1. filtrationthe thus precipitated crystals were filtered
  2. extractionThe resulting filtrate was extracted with ethyl acetate
  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. customBy evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-168ac60ef0c04aa989de80fa72b0a94a
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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