Triethylamine → 6-(1-Decynyl)-2-quinolinecarboxaldehyde

HRID 440419Notes

Reaction equation

HRID 440419 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2.[CH:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>O1CCCC1>[C:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2)#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 129971-DecyneHCID 183731406-Bromoquinoline-2-carbaldehyde

Product 1

HCID 183731216-(1-Decynyl)-2-quinolinecarboxaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-bromo-2-quinolinecarboxaldehyde (18.9 g), 1-decyne (12.2 g) and triethylamine (24.3 g) in dry tetrahydrofuran (300 ml) was chilled to 5° C. and degassed, under nitrogen. bis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which was degassed and stirred under nitrogen at room temperature for 30 mins, and then heated at 40° C. for 19 hrs. The mixture was cooled to room temperature, the precipitate was filtered, and the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel, eluting with heptane to heptane:2% ethyl acetate. The appropriate fractions were collected and evaporated. A 2 g-portion of the residue (23.4 g) was chromatographed, eluting with hexane:dichloromethane/2:1 give 1.3 g (64.0%) of product, mp 46.5°-47.5° C.

Workup

  1. customdegassed, under nitrogen
  2. additionbis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which
  3. customwas degassed
  4. temperatureheated at 40° C. for 19 hrs
  5. temperatureThe mixture was cooled to room temperature
  6. filtrationthe precipitate was filtered
  7. washthe filter cake was washed with ethyl acetate
  8. customthe filtrate was evaporated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated
  14. customThe residue was chromatographed on silica gel
  15. washeluting with heptane to heptane
  16. customThe appropriate fractions were collected
  17. customevaporated
  18. customA 2 g-portion of the residue (23.4 g) was chromatographed
  19. washeluting with hexane

Sources & evidence

ORD record
ord-8b29447749c74cd0a25fd7372c8f10ee
Source dataset
uspto-grants-1996_05
Patent number
US05519062

Reaction notes

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