Benzoyl chloride → 1-methyl-2-phenyl-1H-imidazo[4,5-c]quinoline

HRID 981907Notes

Reaction equation

HRID 981907 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.N>N1C=CC=CC=1.O>[CH3:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 12896473Azane;hydrateHCID 13958346HCID 13958346, compound

Product 1

HCID 100381871-methyl-2-phenyl-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2.1 g (0.012 mole) of crude product of 3-amino-4-methylaminoquinoline was dissolved in 20 ml of pyridine, and 1.5 ml (0.013 mole) of benzoyl chloride was added followed by stirring at room temperature for one hour. The reaction solution was concentrated under reduced pressure, and 20 ml of phosphorus oxychloride was added to the concentrate, followed by refluxing with heating for 3 hours. The residues obtained by concentration under reduced pressure were dissolved in water and the solution was made alkaline with ammonia water. The precipitate was collected by filtration, washed with water and purified by silica gel column chromatography (eluting solvent: chloform/methanol=30/1), to afford 2.1 g of Compound a.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and 20 ml of phosphorus oxychloride
  2. additionwas added to the concentrate
  3. temperatureby refluxing
  4. temperaturewith heating for 3 hours
  5. customThe residues obtained by concentration under reduced pressure
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. custompurified by silica gel column chromatography (eluting solvent: chloform/methanol=30/1)

Sources & evidence

ORD record
ord-1fd4e3b96b9c466a83b50ae38bd80e07
Source dataset
uspto-grants-1991_02
Patent number
US04994468

Reaction notes

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