Quinoline → 2,7-bis(N-phenylacetylamino)dibenzodioxin

HRID 905536Notes

Reaction equation

HRID 905536 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:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].N1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)C=CC=1>[Cu]I.O.C(Cl)Cl>[C:24]1([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:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)[CH:22]=[CH:21][C:8]=4[O:9][C:10]=3[CH:16]=2)=[O:20])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 7047QuinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 578925072,7-Bis(acetylamino)dibenzodioxin

Product 1

HCID 673890942,7-bis(N-phenylacetylamino)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 34.3 g (0.115 mole) of 2,7-bis(acetylamino)dibenzodioxin, 96.4 g (0.576 mole) of iodobenzene, 48.2 g (0.253 mole) of copper (I) iodide, 63.6 g (0.460 mole) of potassium carbonate, and 1500 ml of quinoline was heated with stirring at 170° C. for 48 hours. The reaction mixture was cooled to room temperature, 500 ml of methylene chloride and 500 ml of water were added, and a precipitate was separated by filtration. To the filtrate was added 500 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 79.4 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 500 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-9374108a7280443e8dba6ab2123f1ac4
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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