Ethanol → 4,7-Diethyl-1,10-phenanthroline

HRID 1456906Notes

Reaction equation

HRID 1456906 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-])=O)[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1)[CH3:2].[CH2:16]([C:18]1C2C(=C(N)C=CC=2)N=[CH:20][CH:19]=1)[CH3:17].C(O)C>O=[Pt]=O.[H][H]>[CH2:1]([C:3]1[C:12]2[C:7](=[C:8]3[C:9](=[CH:10][CH:11]=2)[C:18]([CH2:19][CH3:20])=[CH:16][CH:17]=[N:13]3)[N:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 22102163HCID 22102163, compound2×HCID 22102173HCID 22102173, compound

Product 1

HCID 234238154,7-Diethyl-1,10-phenanthroline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 178418361HCID 178418361, compoundSolvent

Procedure

4-Ethyl-8-nitroquinoline is reduced to 4-ethyl-8-aminoquinoline by catalytic reduction with Adams' catalyst as follows: place a solution of 0.05 moles of 4-ethyl-8-nitroquinoline in 100 ml of rectified spirit (ethyl alcohol) together with 0.1 g of Adams' catalyst (platinum (IV) oxide, available from Aldrich Chemical Co., Inc.) in a hydrogenation flask, and shake in hydrogen. After the theoretical volume of hydrogen is absorbed, filter off the platinum with suction and rinse the reaction vessel with rectified spirits. Evaporate the alcohol from the combined filtrate and washings on a water bath. Dissolve the crude residue in rectified spirits, add a little decolorizing charcoal, boil and filter. Heat the filtrate to boiling, add hot water to initiate crystallization and allow to cool.

Workup

  1. customAfter the theoretical volume of hydrogen is absorbed
  2. filtrationfilter off the platinum with suction
  3. washrinse the reaction vessel with rectified spirits
  4. customEvaporate the alcohol from the combined filtrate and washings on a water bath
  5. dissolutionDissolve the crude residue in rectified spirits
  6. additionadd a little decolorizing charcoal, boil
  7. filtrationfilter
  8. temperatureHeat the filtrate
  9. additionadd hot water
  10. customcrystallization
  11. temperatureto cool

Sources & evidence

ORD record
ord-38fef1699ec6476991e1034533f2869d
Source dataset
uspto-grants-1998_12
Patent number
US05846702

Reaction notes

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