2-(Chloromethyl)quinoline → N-[(4-Methoxyphenyl)sulfonyl]-N-(2-quinolinylmethyl)glycine ethyl ester

HRID 2209703Notes

Reaction equation

HRID 2209703 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])=[O:12])=[CH:7][CH:6]=1.Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])=[O:13])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydrideHCID 3113410HCID 3113410, compound

Product 1

HCID 10573821N-[(4-Methoxyphenyl)sulfonyl]-N-(2-quinolinylmethyl)glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.84 g, 35.0 mmol) in dimethylformamide (120.0 mL), is added ethyl 2-[[4-methoxybenzenesulfonyl]amino]acetate (3.19 g, 11.67 mmol) and 2-(chloromethyl)quinoline (2.62 g, 12.26 mmol), and the reaction is stirred for three days at room temperature. Then, additional Nail (0.46 g, 11.67 mmol) is added, and the reaction is heated to 50° C. for 5 hours. The reaction is cooled to 0° C., quenched with water, and extracted well with ether. The combined organic layers are washed with brine, dried (Na2SO4), and the solvent is removed to give ethyl 2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetate.

Workup

  1. additionThen, additional Nail (0.46 g, 11.67 mmol) is added
  2. temperaturethe reaction is heated to 50° C. for 5 hours
  3. temperatureThe reaction is cooled to 0° C.
  4. customquenched with water
  5. extractionextracted well with ether
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-fff3de083c6642f0b5770b9aa7a2df80
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

Loading…