Toluene → 2-Heptyl-6-(5-ethyl-2-pyrimidinyl)naphthalene

HRID 1381061Notes

Reaction equation

HRID 1381061 reaction equation
[OH-].[Na+].Cl.[CH2:4]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C:21]([NH2:23])=[NH:22])[CH:15]=[CH:14]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:24]1([CH3:30])[CH:29]=[CH:28]C=C[CH:25]=1>CO>[CH2:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]3[N:23]=[CH:30][C:24]([CH2:29][CH3:28])=[CH:25][N:22]=3)[CH:17]=2)[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 23323276HCID 23323276, compound

Product 1

HCID 135313252-Heptyl-6-(5-ethyl-2-pyrimidinyl)naphthaleneYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

NaOH (1.1 g, 26 mmols) was added to anhydrous methanol (40 ml) and dissolved therein by heating to 60° C. with stirring. To the solution was added 6-heptyl-2-naphthalenecarboxamidine hydrochloride (4.0 g, 13 mmols) to prepare a suspension with stirring. To this suspension was dropwise added over one minute a solution obtained by dissolving α-ethyl-β-dimethylaminoacrolein (1.7 g, 13 mmols) in anhydrous methanol (5 ml), followed by gently refluxing the mixture with stirring for 2 hours, distilling off methanol under the atmospheric pressure after completion of the reaction, adding toluene (50 ml) to the residue to extract the resulting product, washing the extraction solution with a 2N-NaOH aqueous solution and then with water, drying over anhydrous sodium sulfate, and distilling off toluene under reduced pressure to obtain solids, which were then recrystallized from ethanol to obtain the objective 2-heptyl-6-(5-ethyl-2-pyrimidinyl)naphthalene (2.5 g, 7.8 mmols) (yield: 60%). M.P.: 62.3°-63.1° C.

Workup

  1. dissolutiondissolved
  2. customto prepare a suspension
  3. stirringwith stirring
  4. additionTo this suspension was dropwise added over one minute a solution
  5. customobtained
  6. temperatureby gently refluxing the mixture
  7. stirringwith stirring for 2 hours
  8. distillationdistilling off methanol under the atmospheric pressure
  9. customafter completion of the reaction
  10. extractionto extract the resulting product
  11. washwashing the extraction solution with a 2N-NaOH aqueous solution
  12. dry with materialwith water, drying over anhydrous sodium sulfate
  13. distillationdistilling off toluene under reduced pressure
  14. customto obtain solids, which
  15. customwere then recrystallized from ethanol

Sources & evidence

ORD record
ord-d593f3f4dc2447a4b3d428c7e9c53007
Source dataset
uspto-grants-1986_04
Patent number
US04585575

Reaction notes

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