Triethylamine → 4-Chloro-8-vinyl-quinoline

HRID 505857Notes

Reaction equation

HRID 505857 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[Cl:12].[CH2:13](N(CC)CC)[CH3:14]>C(O)C>[Cl:12][C:7]1[C:6]2[C:11](=[C:2]([CH:13]=[CH2:14])[CH:3]=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 124036918-Bromo-4-chloroquinoline

Product 1

HCID 687181654-Chloro-8-vinyl-quinolineYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 975 mg (4.02 mmol) 8-bromo-4-chloroquinoline (commercially available from Ubichem Research Ltd, Budapest, Hungary), 166 mg (0.20 mmol) PdCl2dppfCH2Cl2, 833 mg (6.00 mmol) potassium vinyl tetrafluoroborate and 0.57 ml (4.10 mmol) triethylamine in 20 ml ethanol was heated at reflux for 3 h. The resulting yellow suspension was filtered and the filtrate evaporated to dryness. The residue was suspended in ethyl acetate, filtered and the filtrate extracted with water. The organic layer was evaporated to dryness and the isolated crude product purified by silica gel chromatography (hexane/ethyl acetate 9:1) to yield 207 mg (27%) of the title compound as white crystals. MS: 189.1 (M+). 1H-NMR (300 MHz, CDCl3): 5.53 (d, J=11.1 Hz, 1H); 5.95 (d, J=17.7 Hz, 1H); 7.51 (d, J=4.6 Hz. 1H); 7.63 (t, J=7.9 Hz, 1H); 7.96 (dd, J=17.7, 11.1 Hz, 1H); 7.97 (d, J=7.1 Hz, 1H); 8.19 (d, J=8.5 Hz, 1H); 8.80 (d, J=4.6 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe resulting yellow suspension was filtered
  4. customthe filtrate evaporated to dryness
  5. filtrationfiltered
  6. extractionthe filtrate extracted with water
  7. customThe organic layer was evaporated to dryness
  8. customthe isolated crude product
  9. custompurified by silica gel chromatography (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-c1c5a42efa814c3cb587e0d5952647f7
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

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