Water → N-[2-(2-chloro-6-methoxyquinolin-4-yl)ethyl]acetamide

HRID 725887Notes

Reaction equation

HRID 725887 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:15]=[C:14]([CH2:16][CH2:17][NH2:18])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1.C(N(CC)CC)C.O>O1CCCC1>[Cl:5][C:6]1[CH:15]=[C:14]([CH2:16][CH2:17][NH:18][C:1](=[O:3])[CH3:2])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 197099622-(2-Chloro-6-methoxyquinolin-4-yl)ethylamine

Product 1

HCID 9860467N-[2-(2-chloro-6-methoxyquinolin-4-yl)ethyl]acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.37 g, 4.7 mmol) was added dropwise gradually under ice-cooling to a solution of 2-(2-chloro-6-methoxyquinolin-4-yl)ethylamine (1.0 g, 4.2 mmol) and triethylamine (0.87 g, 8.6 mmol) in tetrahydrofuran (50 ml). The reaction mixture was stirred at room temperature for 1 hour and poured into water. The organic materials were extracted with a mixed solvent of 5% methanol/ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to obtain the title compound (0.96 g, 80%).

Workup

  1. extractionThe organic materials were extracted with a mixed solvent of 5% methanol/ethyl acetate
  2. washThe extract was washed with saturated brine and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-de12fc1d39fe45c5a2e185fa1e24afec
Source dataset
uspto-grants-1998_01
Patent number
US05708005

Reaction notes

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