Water → N-(4-Chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067997Notes

Reaction equation

HRID 1067997 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][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]([I:21])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].O>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]([I:21])[CH:17]=3)[N:12]([CH3:24])[CH:11]=2)=[O:9])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178522879HCID 178522879, compound

Product 1

HCID 21192528N-(4-Chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide (12.07 g) from Preparation No. 4 and potassium carbonate (5.70 g) are disolved in DMF (90 mL). lodomethane (2.1 mL) is added and the mixture is stirred at room temperature for 1 h. The resulting suspension is poured into water (500 mL) and filtered. The crude solid is washed with water (50 mL) and diethyl ether (100 mL) and then is recrystallized from ethanol to afford 10.6 g (85%) of the title compound as a white solid.

Workup

  1. additionlodomethane (2.1 mL) is added
  2. filtrationfiltered
  3. washThe crude solid is washed with water (50 mL) and diethyl ether (100 mL)
  4. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-0d71b6dcdc7a462497e4b55fb160fddf
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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