Ethyl Acetate → N-(4-Chlorobenzyl)-6-(3-hydroxy-1-propynyl)-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxamide

HRID 1067964Notes

Reaction equation

HRID 1067964 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:34][CH2:35][CH3:36].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:34][CH2:35][CH3:36])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178522861HCID 178522861, compound

Product 1

HCID 21192522N-(4-Chlorobenzyl)-6-(3-hydroxy-1-propynyl)-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxamideYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.50 g of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5, potassium carbonate (0.76 g), and 1-iodopropane (0.47 g) in DMF is heated to 100° C. for 6 hrs and stirred at room temperature overnight. The reaction mixture is filtered, and the solvent is evaporated at reduced pressure leaving a light brown solid. The solid is stirred with ethyl acetate for an hour and filtered. The solvent is evaporated from the filtrate under reduced pressure, leaving 0.12 g of the title compound as a yellowish-white solid.

Workup

  1. customfrom Preparation No
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent is evaporated at reduced pressure
  4. customleaving a light brown solid
  5. filtrationfiltered
  6. customThe solvent is evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-a5619edf7061406880b1bc03512ec7c1
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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