Quinoline → HCID 68812092, compound

HRID 1821149Notes

Reaction equation

HRID 1821149 reaction equation
[C:1]([NH:4][C:5]1[CH:22]=[CH:21][C:8]2[O:9][C:10]3[C:16]([NH:17][C:18](=[O:20])[CH3:19])=[CH:15][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:1]([N:4]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:5]1[CH:22]=[CH:21][C:8]2[O:9][C:10]3[C:16]([N:17]([C:18](=[O:20])[CH3:19])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 7047QuinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 68812137HCID 68812137, compound

Product 1

HCID 68812092HCID 68812092, compound

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 N,N′-diacetyl-2,6-diaminodibenzodioxin, 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 slurry was cooled to room temperature, 500 ml of methylene chloride and 500 ml of water were added, and a precipitate was filtered off. 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. The product was used without purification in the next reaction.

Workup

  1. temperaturewas heated
  2. temperatureThe slurry was cooled to room temperature
  3. filtrationa precipitate was filtered off
  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-3a0848a8324c447a98293dbd204d12c9
Source dataset
uspto-grants-2009_10
Patent number
US07605277B2

Reaction notes

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