Quinoline → 2,5-bis(4-cyanophenyl)furan

HRID 1450528Notes

Reaction equation

HRID 1450528 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[CH:11][C:12]=2C(O)=O)=[CH:4][CH:3]=1.[C:23]([Cu])#[N:24].[N:26]1C2C(=CC=CC=2)C=C[CH:27]=1>Cl>[C:27]([C:19]1[CH:18]=[CH:17][C:16]([C:10]2[O:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([C:23]#[N:24])=[CH:7][CH:6]=3)=[CH:12][CH:11]=2)=[CH:21][CH:20]=1)#[N:26]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 19977168HCID 19977168, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 6229852,5-bis(4-cyanophenyl)furanYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2,5-bis(4-bromophenyl)-3-furan carboxylic acid 0.85 g (0.002 mole), CuCN 0.45 g (0.005 mole) in 10 ml freshly distilled quinoline is heated under reflux for 3 hours. The mixture is cooled and 100 ml dilute aqueous HCl is added and the mixture is stirred for 30 min. and filtered. The solid is washed with water and then with hexane. The resultant yellow solid is dissolved in acetone and passed through an alumina (neutral) column to yield a yellow crystalline solid 0.37 g (68%) having amp of 293°-295° C. The product is identical with that described in Example 1.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washThe solid is washed with water
  6. dissolutionThe resultant yellow solid is dissolved in acetone

Sources & evidence

ORD record
ord-783162db3dff460eb7812e83cb60089d
Source dataset
uspto-grants-1997_02
Patent number
US05602172

Reaction notes

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