4-Chlorophenol → 1,2,3-Benzotriazin-4(3H)-one, 6-(4-chlorophenoxy)-3-(3-pyridinylmethyl)-

HRID 1609582Notes

Reaction equation

HRID 1609582 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:7](=[O:18])[C:6]=2[CH:19]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2]2[CH:3]=[CH:4][C:5]3[N:10]=[N:9][N:8]([CH2:11][C:12]4[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=4)[C:7](=[O:18])[C:6]=3[CH:19]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 57142821HCID 57142821, compound

Product 1

HCID 2163331,2,3-Benzotriazin-4(3H)-one, 6-(4-chlorophenoxy)-3-(3-pyridinylmethyl)-Yield 49.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10.0 g of 6-bromo-3-(3-pyridylmethyl)-1,2,3-benzotriazin-4 (3H)-one, 6.1 g of 4-chlorophenol, 9.4 g of cupric oxide, 13.1 g of potassium carbonate and 100 ml of pyridine was refluxed under heating for 9 hours. After finishing the reaction, the insoluble material was filtered off, and the filtrate was concentrated in vacuo. The resulting residue was chromatographed on a column of silica gel, developing with ethyl acetate/hexane=1:1 and then recrystallized from hexane-methylene chloride to give 5.68 g of the titled compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 9 hours
  3. customthe reaction
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting residue was chromatographed on a column of silica gel
  7. customrecrystallized from hexane-methylene chloride

Sources & evidence

ORD record
ord-2256b1b3e1fc4a93b19cb107e232dbcb
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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