HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1067982
Notes
Print preview

Reaction equation

HRID 1067982 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 14202443Ethanol, 1-bromo-HCID 178522861HCID 178522861, compound

Product 1

HCID 16073849N-[(4-chlorophenyl)methyl]-1-(2-hydroxyethyl)-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (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

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

Sources & evidence

ORD record
ord-64f85f9bab434f52a2e39a49ae7f1d3f
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248739B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes