Styrene → 4-(2-Phenylethenyl)-7-chloroquinoline

HRID 1953451Notes

Reaction equation

HRID 1953451 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>[C:15]1([CH:14]=[CH:13][C:2]2[C:11]3[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 7501StyreneHCID 109776384-Bromo-7-chloroquinoline

Product 1

HCID 540730574-(2-Phenylethenyl)-7-chloroquinolineYield 51%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-7-chloroquinoline (24.3 g, 0.1 mol), styrene (12.0 g, 0.125 mol), tri(o-tolyl) phosphine (0.4 g, 1.3 mmol), palladium acetate (0.2 g, 0.89 mol) and triethylamine (120 mls) was charged into a 300 ml stirred pressure vessel and heated at 120° C. for 17 hours. The mixture was cooled, filtered to remove triethylamine hydrobromide, and the solids washed with ethyl acetate (250 ml). Solvents were evaporated under reduced pressure and the residue dissolved in ethyl acetate (500 ml). The solution was washed with water and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallisation of the residue from ethyl acetate: hexane gave the product (13.5 g, 51%) as an orange solid, mp 120-122° C.

Workup

  1. additionwas charged into a 300 ml
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customto remove triethylamine hydrobromide
  5. washthe solids washed with ethyl acetate (250 ml)
  6. customSolvents were evaporated under reduced pressure
  7. dissolutionthe residue dissolved in ethyl acetate (500 ml)
  8. washThe solution was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulphate
  10. customEvaporation of the solvent
  11. customunder reduced pressure and recrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-a15e52292be44c5e8a92dd8d8f534d83
Source dataset
uspto-grants-2000_09
Patent number
US06117884

Reaction notes

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