p-Bromochlorobenzene → 7-(4-chlorophenoxy)-3,4-dihydro-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

HRID 1609594Notes

Reaction equation

HRID 1609594 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([CH2:13][C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[C:9]3=[O:12])=[CH:4][CH:3]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 11430Potassium CarbonateHCID 542355103,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone

Product 1

HCID 152304757-(4-chlorophenoxy)-3,4-dihydro-2-(3-pyridylmethyl)-1 (2H)-isoquinolinoneYield 61.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.97 g of 3,4-dihydro-7-hydroxy-2-(3-pyridylmethyl)-1 (2H)-isoquinolinone, 4.50 g of 4-bromochlorobenzene, 3.88 g of cupric oxide, 5.39 g of potassium carbonate and 30 ml of pyridine was refluxed under heating for 20 hours. After finishing the reaction, the insoluble material was filtered, and the filtrate was concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate to give 4.39 g of the titled compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 20 hours
  3. customthe reaction
  4. filtrationthe insoluble material was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was chromatographed on a column of silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-016bb8a169ba4835a6a6e722e7ddd305
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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