Potassium Carbonate → HCID 15230481, compound

HRID 1609585Notes

Reaction equation

HRID 1609585 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[O:19].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu].ClC1C=CC=CC=1Cl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[N:6]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:5]3=[O:19])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 2855718-Crown-6HCID 11821097HCID 11821097, compound

Product 1

HCID 15230481HCID 15230481, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 260 mg of 5-amino-2-(3-pyridylmethyl)-1H-isoindole-1,3-(2H)-dione, 296 mg of 1-chloro-4-iodobenzene, 131 mg of copper dust, 54 mg of 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane), 569 mg of potassium carbonate and 4 ml of 1,2-dichlorobenzene was refluxed under heating for 1 hour. After finishing the reaction, the insoluble material was filtered off, and the filtrate was concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with chloroform and methanol (20:1) to give 185 mg of the titled compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1 hour
  3. customthe reaction
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was chromatographed on a column of silica gel
  7. washeluting with chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-b7aead8787aa4cd58e3bbd617f18e41b
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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