Triethylamine → 2-Methyl-8-vinyl-quinoline

HRID 505858Notes

Reaction equation

HRID 505858 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[CH2:13](N(CC)CC)[CH3:14]>C(O)C>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH:13]=[CH2:14])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 47150308-Bromo-2-methylquinoline

Product 1

HCID 213946562-Methyl-8-vinyl-quinolineYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4.80 g (21.60 mmol) 8-bromo-2-methylquinoline (commercially available from ACB Block Ltd, Moscow, Russia), 0.89 g (1.10 mmol) PdCl2dppfCH2Cl2, 4.48 g (32.40 mmol) potassium vinyl tetrafluoroborate and 3.10 ml (22.10 mmol) triethylamine in 150 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 (CH2Cl2/ethyl acetate 98:2) to yield 2.68 g (73%) of the title compound as a colorless oil. MS: 169.1 (M+). 1H-NMR (300 MHz, CDCl3): 2.74 (s, 1H); 5.47 (dd, J=11.1, 1.6 Hz, 1H); 5.97 (dd, 17.9, 1.6 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H); 7.43 (t, J=7.7 Hz, 1H); 7.66 (dd, J=8.1, 1.2 Hz, 1H); 7.87 (dd, J=7.3, 1.2 Hz, 1H); 7.97 (d, J=8.4 Hz, 1H); 8.05 (dd, J=17.9, 11.1 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 (CH2Cl2/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-33f608dc784e42fa93811542031822df
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

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