Hydrochloric Acid → HCID 21186672, compound

HRID 1384264Notes

Reaction equation

HRID 1384264 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]CC)=[O:14].Cl>[OH-].[Na+]>[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]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21186750HCID 21186750, compound

Product 1

HCID 21186672HCID 21186672, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (3.05 g, 13.1 mmol) was suspended in 5% sodium hydroxide aqueous solution (20.0 ml) and heated under reflux for 1 hour. After cooling to room temperature, this was adjusted to pH 4 by adding concentrated hydrochloric acid and extracted with chloroform-methanol (4:1) mixed solvent. The thus obtained organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent under reduced pressure, the title compound (1.95 g, 72.7%) was obtained as pale brown powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with chloroform-methanol (4:1)
  4. additionmixed solvent
  5. washThe thus obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customBy evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-76ceae29ce494296ab4dbf8d8c16e20a
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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