Benzene, 1-(chloromethyl)-2-fluoro- → 1-[4-(2-Fluorophenylmethyl)amino-2-methyl-3-quinolinyl]-ethanone

HRID 1904966Notes

Reaction equation

HRID 1904966 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13](=[O:15])[CH3:14].[OH-].[K+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Cl>CS(C)=O.O>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 14797Potassium HydroxideHCID 6722971-(4-Amino-2-methylquinolin-3-yl)ethanone

Product 1

HCID 143906181-[4-(2-Fluorophenylmethyl)amino-2-methyl-3-quinolinyl]-ethanone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent

Procedure

A solution of 1-(4-amino-2-methyl-3-quinolinyl)-ethanone in dimethylsulfoxide (150 ml) was added to a stirred slurry of pulverized 85% potassium hydroxide (7 g) in dimethylsulfoxide (40 ml). This mixture was stirred at ambient temperature for twenty minutes, and thereafter a solution of o-fluorobenzylchloride (15.2 g) in dimethylsulfoxide (40 ml) was added dropwise. The mixture was stirred for two hours and allowed to stand overnight at room temperature. Thereafter, it was poured onto ice and diluted with water to form a tacky lump. This was allowed to stand for fifteen minutes, and the aqueous dimethylsulfoxide was decanted. The tacky precipitate was dissolved in dichloromethane, washed with water (3×) and saturated sodium chloride solution, and dried over sodium sulfate. Removal of the sodium sulfate by filtration and the solvent by evaporation gave 26.5 g of viscous oil.

Workup

  1. stirringThe mixture was stirred for two hours
  2. additionThereafter, it was poured onto ice
  3. customto form a tacky lump
  4. waitto stand for fifteen minutes
  5. customthe aqueous dimethylsulfoxide was decanted
  6. dissolutionThe tacky precipitate was dissolved in dichloromethane
  7. washwashed with water (3×) and saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the sodium sulfate
  10. filtrationby filtration
  11. customthe solvent by evaporation

Sources & evidence

ORD record
ord-21471c709def467a9f02520188ccefbd
Source dataset
uspto-grants-1989_06
Patent number
US04840972

Reaction notes

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