Methane → 4-Ethyl-4-phenyl-2-(2-phenylquinolin-4-yl)-imidazoline

HRID 2227454Notes

Reaction equation

HRID 2227454 reaction equation
[C:1]1([C:7]([NH2:12])([CH2:10][CH3:11])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.C.CO[C:20]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[C:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:23]=1)=O>C1(C)C=CC=CC=1.CO.C(Cl)Cl.O>[CH2:10]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][NH:9][C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:23]=2)=[N:12]1)[CH3:11]

Participants

9

Reactant 4

HCID 297MethaneHCID 211492-Phenylbutane-1,2-diamineHCID 609693Methyl 2-phenyl-4-quinolinecarboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 1784352444-Ethyl-4-phenyl-2-(2-phenylquinolin-4-yl)-imidazoline

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent3×HCID 6344DichloromethaneSolvent

Procedure

2-Phenylbutane-1,2-diamine (328 mg, 2.0 mmol) in 4.4 mL of toluene is added dropwise to a stirred solution of trimethylaluminum (2.0 M, 1 mL) in 5 mL of toluene at below 10° C. under nitrogen. At the end of methane evolution, methyl-2-phenyl-4-quinolinecarboxylate (263 mg, 1 mmol) in 2 mL of toluene is gradually added at room temperature. The reaction mixture is refluxed for 3 hours under nitrogen. After cooling, the solution is treated with 1 mL of water, diluted with 1 mL of methanol and 1 mL of methylene chloride, and refluxed for 15 minutes. After separation of organic solvent and solvent evaporation, the residue is purified over silica gel chromatography eluting with 5-10% MeOH/CH2Cl2. The corresponding compound is obtained as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours under nitrogen
  2. temperatureAfter cooling
  3. temperaturerefluxed for 15 minutes
  4. customAfter separation of organic solvent and solvent evaporation
  5. customthe residue is purified over silica gel chromatography
  6. washeluting with 5-10% MeOH/CH2Cl2
  7. customThe corresponding compound is obtained as a white solid

Sources & evidence

ORD record
ord-3653a529e44440ccb38978cef2f77d49
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

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