Dichloromethane → N-[(4-chlorophenyl)methyl]-1-(2-hydroxyethyl)-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

HRID 1067257Notes

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+].Br[CH:34]([OH:36])[CH3:35].ClCCl>O.CO>[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]([CH2:35][CH2:34][OH:36])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 4 (0.37 g) is added potassium carbonate (2.75 g) and bromoethanol (0.71 mL). The flask is tightly capped and heated to 100° C. After 4 hours the reaction is cooled to room temperature and partioned between dichloromethane containing methanol and water. The organic layer is washed with two additional portions of water, brine, dried and concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% to 10% methanol in dichloromethane to afford 0.09 g of the title compound as a white solid.

Workup

customfrom Preparation No
customThe flask is tightly capped
temperatureAfter 4 hours the reaction is cooled to room temperature
washThe organic layer is washed with two additional portions of water, brine
customdried
concentrationconcentrated under reduced pressure
customchromatographed on silica eluting with 2% to 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-66c740322666462483f3b8642ba31c16
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248736B1

Reaction notes

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