Methyl iodide → N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamide

HRID 1067259Notes

Reaction equation

HRID 1067259 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:27](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[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]([CH3:27])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522861HCID 178522861, compound

Product 1

HCID 11740538N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 6.90 g of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 4, 10.4 g of potassium carbonate, and 2.3 mL of methyl iodide in 40 mL of DMF is stirred at 90° C. for 4 hours, then cooled and diluted with 350 mL of water. The resulting solid is filtered, washed well with water, and dried under vacuum. Flash chromatography of the solid on silica using 3-5% methanol in dichloromethane provides 6.02 g of the title compound as a solid.

Workup

  1. customfrom Preparation No
  2. temperaturecooled
  3. filtrationThe resulting solid is filtered
  4. washwashed well with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-24b5e9ba89e44a6ebca526b8ac1c6414
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

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