Quinoline → 4-(4-Cyanophenyl)-2,6-dimethylquinoline

HRID 1581454Notes

Reaction equation

HRID 1581454 reaction equation
N1C2C(=CC=CC=2)C=CC=1.Br[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=2)[N:15]=[C:14]([CH3:23])[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].[C:30]([C:32]1[CH:37]=[CH:36][C:35](OB(O)O)=[CH:34][CH:33]=1)#[N:31]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CO.C1(C)C=CC=CC=1>[C:30]([C:32]1[CH:37]=[CH:36][C:35]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=3)[N:15]=[C:14]([CH3:23])[CH:13]=2)=[CH:34][CH:33]=1)#[N:31]

Participants

9

Reactant 4

HCID 7047QuinolineHCID 10340Sodium CarbonateHCID 149913604-Bromo-2,6-dimethylquinolineHCID 220496434-Cyanophenylboric acid

Product 1

HCID 227214744-(4-Cyanophenyl)-2,6-dimethylquinolineYield 88.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

In example 1-6, a compound represented by the chemical formula (38) was synthesized through the following processes as an example quinoline derivative. First, a solution in which 4-bromo-2,6-dimethylquinoline (1.05 g) identical to that in the example 1-4 and Pd(Ph3P)4 (0.31 g) were added to toluene (8.5 ml), a solution in which Na2CO3 (1.81 g) was added to water (8.5 ml), and a solution in which 4-cyanophenylboric acid (0.726 g) was added to methanol (2.8 ml) were mixed and allowed to react for 22 hours in a nitrogen atmosphere at a temperature of 80° C. The reaction solution was poured into water and extracted using chloroform. The chloroform layer was dried using Na2SO4 and the Na2SO4 was removed by filtering. The solvent was removed under reduced pressure and the residue was purified through column chromatography (silica gel, hexane/ethyl acetate=2/1) to obtain 4-(4-cyanophenyl)-2,6-dimethylquinoline (1.013 g) represented by the following chemical formula (48).

Workup

  1. additionwere mixed
  2. customto react for 22 hours in a nitrogen atmosphere at a temperature of 80° C
  3. extractionextracted
  4. dry with materialThe chloroform layer was dried
  5. customthe Na2SO4 was removed
  6. filtrationby filtering
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified through column chromatography (silica gel, hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-8666f5c35acb4f6c86c8a440dabafe8f
Source dataset
uspto-grants-2004_05
Patent number
US06730418B2

Reaction notes

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