Methyl iodide → 1-Methyl-3-[N-(2-{[1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolyl]acetoxy}ethyl)carbamoyl]pyridinium iodide

HRID 1494187Notes

Reaction equation

HRID 1494187 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([O:22][CH2:23][CH2:24][NH:25][C:26]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:27])=[O:21])=[C:9]2[CH3:34])=[O:7])=[CH:4][CH:3]=1.[CH3:37][I:38]>CC(C)=O>[I-:38].[CH3:37][N+:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:26](=[O:27])[NH:25][CH2:24][CH2:23][O:22][C:20](=[O:21])[CH2:19][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:36][CH:35]=3)[C:9]=2[CH3:34])[CH:29]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 15680016N-(2-{[1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indolyl]acetoxy}ethyl)-3-pyridinecarboxamide

Product 1

HCID 156800191-Methyl-3-[N-(2-{[1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolyl]acetoxy}ethyl)carbamoyl]pyridinium iodideYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The quaternization of the indomethacin ester prepared in Example 93 (0.50 g, 1.0 mmol) was carried out in acetone, using methyl iodide (1.7 g, 12 mmol). The reaction was refluxed overnight. The solvent was removed under reduced pressure and a yellow solid was obtained. The product was recrystallized using ethanol and a very small amount of ether. Small mold-like crystals were obtained which were light yellow in color. The reaction gave 0.43 g or a 66% yield of the purified material; mp 178°-179° C. UV, NMR and elemental analyses confirmed that the product had the structural formula: ##STR124##

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. customa yellow solid was obtained
  4. customThe product was recrystallized
  5. customSmall mold-like crystals were obtained which
  6. customThe reaction gave 0.43 g

Sources & evidence

ORD record
ord-f17cb2dabcb24180ab1cda8d06e795da
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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