Ethoxyacetyl chloride → HCID 57429982, compound

HRID 2105477Notes

Reaction equation

HRID 2105477 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][CH:15]=[CH:14][CH:13]=2>ClCCl>[Cl:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:8][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chloride2×HCID 8173324-chloroquinolin-3-amine

Product 1

HCID 57429982HCID 57429982, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of ethoxyacetyl chloride (4.2 g, 34 mmol) in dichloromethane was added dropwise to a stirred solution of 3-amino-4-chloroquinoline (5.1 g, 29 mmol) in dichloromethane (75 mL), and the reaction was stirred for one hour at room temperature. Additional ethoxyacetyl chloride (0.5 g, 4 mmol) was added, and the reaction was stirred for 30 minutes and diluted with dichloromethane (75 mL). The resulting mixture was washed with saturated aqueous sodium bicarbonate (50 mL), dried over potassium carbonate, and filtered. Methanol was added to facilitate the filtration. The filtrate was concentrated under reduced pressure to provide 7.3 g of N-(4-chloroquinolin-3-yl)-2-ethoxyacetamide as a dark solid.

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. washThe resulting mixture was washed with saturated aqueous sodium bicarbonate (50 mL)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. additionMethanol was added
  6. filtrationthe filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e3f414f7cef43829d260a441d4acb6e
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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