Acrolein → HCID 3593281, compound

HRID 405663Notes

Reaction equation

HRID 405663 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:16](=O)[CH:17]=[CH2:18].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[N:1]1[C:2]2[C:15](=[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]3=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7847AcroleinHCID 136959-AminophenanthreneHCID 14798Sodium Hydroxide

Product 1

HCID 3593281HCID 3593281, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

2.52 g of 9-aminophenanthrene (13 mmol) was added into a two-necked bottle and placed in a drying oven. After 2.1 g of ferric chloride (13 mmol) and 1.77 g of zinc chloride (13 mmol) were added, a nitrogen gas was conducted. Next, 25 ml of acetic acid was slowly added. Next, 875 mg of propenal (15.6 mmol) was then added with thermal reflux for three hours. After cooling, 15% of the NaOH aqueous solution was slowly added under an ice bath to neutralize the pH level to 7. Next, the resulting solution was extracted by adding ethyl acetate and a saturated NaHCO3 aqueous solution. Following, water was removed by adding dried magnesium sulfate and solvent was removed by using filtration and concentration processes. The result was next purified using column chromatography using n-hexane/ethyl acetate (4:1) as an eluent. 1.0 g of a white dibenzo[h,f]quinoline (DBQ) solid was obtained, with a yield of 34%.

Workup

  1. customplaced in a drying oven
  2. temperaturethermal reflux for three hours
  3. temperatureAfter cooling
  4. extractionNext, the resulting solution was extracted
  5. additionby adding ethyl acetate
  6. customwater was removed
  7. additionby adding dried magnesium sulfate and solvent
  8. customwas removed
  9. filtrationfiltration and concentration processes
  10. customThe result was next purified

Sources & evidence

ORD record
ord-03864e4d77ae4a219b15510391646dce
Source dataset
uspto-grants-2014_06
Patent number
US08753756B2

Reaction notes

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