Methacrolein → HCID 59629733, compound

HRID 405664Notes

Reaction equation

HRID 405664 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.[CH3:16][C:17](=[CH2:20])[CH:18]=O.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH3:20][C:17]1[CH:16]=[N:1][C:2]2[C:15]([CH:18]=1)=[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=[C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=21

Participants

6

Reactant 3

HCID 6562MethacroleinHCID 136959-AminophenanthreneHCID 14798Sodium Hydroxide

Product 1

HCID 59629733HCID 59629733, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

1.58 g of 9-aminophenanthrene (8.2 mmol) was added into a two-necked bottle and placed in a drying oven. After 1.33 g of ferric chloride (8.2 mmol) and 1.12 g of zinc chloride (8.2 mmol) were added, a nitrogen gas was conducted. Next, 18 ml of acetic acid was slowly added. 690 mg of methyl propenal (9.8 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. 817 mg of a white 3-methyl dibenzo[h,f]quinoline (3 mDBQ) solid was obtained, with a yield of 41%.

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-3eb88d92be8d4b57a6ada0126a41dbff
Source dataset
uspto-grants-2014_06
Patent number
US08753756B2

Reaction notes

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