Triethylamine → N-(Quinolin-3-Yl)propanamide

HRID 1975766Notes

Reaction equation

HRID 1975766 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C(N(CC)CC)C>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 113753-AminoquinolineHCID 62324Propionyl chloride

Product 1

HCID 19032664N-(Quinolin-3-Yl)propanamideYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Propionic acid chloride (17 g, 184 mmol) was added at ambient temperature to a solution of 25 g (174 mmol) 3-aminoquinoline and 26 ml triethyl amine in 400 ml dichloromethane. After stirring for 2 hours in 200 ml 10% sodium carbonate was added and the mixture was shaken and separated. The aqueous phase was extracted 3 times with dichloromethane and 3 times with ethyl acetate. The combined organic phases where dried (magnesium sulfate), filtered and evaporated to yield 35.0 g (100%) of the desired product.

Workup

  1. additionwas added
  2. customseparated
  3. extractionThe aqueous phase was extracted 3 times with dichloromethane and 3 times with ethyl acetate
  4. dry with materialThe combined organic phases where dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-52d376c82de4446989b8d6196646b5a8
Source dataset
uspto-grants-1994_02
Patent number
US05288748

Reaction notes

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