Sodium Hydroxide → HCID 70226761, compound

HRID 1384278Notes

Reaction equation

HRID 1384278 reaction equation
[N+:1]([O-:21])([O:3][CH:4]1[C:10]2=[N:11][C:12]([CH3:20])=[C:13]([C:15]([O:17]CC)=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:2].[OH-].[Na+]>CO>[N+:1]([O-:21])([O:3][CH:4]1[C:10]2=[N:11][C:12]([CH3:20])=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21186782HCID 21186782, compound

Product 1

HCID 70226761HCID 70226761, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Ethoxycarbonyl-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl) nitrate (1.51 g, 5.12 mmol) was dissolved in methanol (24.0 ml) to which was subsequently added dropwise 10% sodium hydroxide aqueous solution (6.0 ml) at 0° C. After 1.5 hours of stirring at room temperature, the solvent was evaporated and the thus obtained residue was washed with ethyl acetate, adjusted to pH 6 with 2 N hydrochloric acid and then extracted with chloroform:methanol (5:1). The thus obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. By evaporating the solvent under reduced pressure, the title compound (1.07 g, 78.5%) was obtained as pale yellow amorphous.

Workup

  1. customthe solvent was evaporated
  2. washthe thus obtained residue was washed with ethyl acetate
  3. extractionextracted with chloroform:methanol (5:1)
  4. washThe thus obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customBy evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-2a82294118f64aafb96b2f64aa94edd5
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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