Benzaldehyde → HCID 21186745, compound

HRID 1384282Notes

Reaction equation

HRID 1384282 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].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH:18](=[C:8]1/[CH2:9][CH2:10][CH2:11][CH2:12][C:5]2[C:6]/1=[N:7][C:2]([CH3:1])=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=2)/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 21186750HCID 21186750, compound

Product 1

HCID 21186745HCID 21186745, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.07 g, 4.40 mmol) and benzaldehyde (583.6 mg, 5.50 mmol) were dissolved in acetic anhydride (2.0 ml), and the solution was mixed with zinc chloride (40.0 mg, 0.30 mmol) at room temperature and then heated under reflux for 36 hours. After cooling, acetic anhydride was evaporated under reduced pressure, and the thus obtained residue was mixed with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:6-1:5) to obtain the title compound (471.4 mg, 33.4%) as pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 36 hours
  3. temperatureAfter cooling
  4. customacetic anhydride was evaporated under reduced pressure
  5. additionthe thus obtained residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  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=1:6-1:5)

Sources & evidence

ORD record
ord-5b670901d5d843159f95704ab0e21504
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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