Quinoline → 2,7-bis(N-3-pyridylacetylamino)dibenzodioxin

HRID 905537Notes

Reaction equation

HRID 905537 reaction equation
[C:1]([NH:4][C:5]1[CH:22]=[CH:21][C:8]2[O:9][C:10]3[CH:16]=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=[CH:13][C:11]=3[O:12][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].I[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[N:36]1[C:45]2[C:40](=CC=CC=2)[CH:39]=[CH:38][CH:37]=1>[Cu]I.O.C(Cl)Cl>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:19][C:18]([NH:17][C:15]2[CH:14]=[CH:13][C:11]3[O:12][C:7]4[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH2:2][C:38]5[CH:37]=[N:36][CH:45]=[CH:40][CH:39]=5)[CH:22]=[CH:21][C:8]=4[O:9][C:10]=3[CH:16]=2)=[O:20])[CH:25]=1

Participants

8

Reactant 4

HCID 7047QuinolineHCID 11430Potassium CarbonateHCID 707143-IodopyridineHCID 578925072,7-Bis(acetylamino)dibenzodioxin

Product 1

HCID 673893532,7-bis(N-3-pyridylacetylamino)dibenzodioxin

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

A slurry prepared from 7.0 g (0.023 mole) of 2,7-bis(acetylamino)dibenzodioxin, 12.0 g (0.059 mole) of 3-iodopyridine, 9.8 g (0.051 mole) of copper (I) iodide, 12.9 g (0.093 mole) of potassium carbonate, and 230 ml of quinoline was heated with stirring at 170° C. for 48 hours. The reaction mixture was cooled to room temperature, 100 ml of methylene chloride and 100 ml of water were added, and a precipitate was separated by filtration. To the filtrate was added 100 ml of water and the organic layer was separated from the aqueous layer. The organic layer was concentrated and dried under reduced pressure to give 23.5 g of a crude product which was used without purification in the next reaction.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customa precipitate was separated by filtration
  4. additionTo the filtrate was added 100 ml of water
  5. customthe organic layer was separated from the aqueous layer
  6. concentrationThe organic layer was concentrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-0ab7ca54bcbc4db89a8e7dd6e3a56049
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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