Propargyl alcohol → 3-(8-Isoquinolinyl)-2-propyn-1-ol

HRID 1651104Notes

Reaction equation

HRID 1651104 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:14]#[C:13][CH2:12][OH:15])[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 98591348-Bromoisoquinoline

Product 1

HCID 143474813-(8-Isoquinolinyl)-2-propyn-1-ol

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere, 0.068 g of bis(triphenylphosphine)palladium dichloride and 0.013 g of cuprous iodide was added with stirring to a deoxygenated solution of 1 g of 8-bromoisoquinoline, 0.56 mL of propargyl alcohol and 2 mL of triethylamine in 25 mL of dichloromethane. The mixture was stirred at room temperature for 2 hours and then at reflux for 20 hours. The cooled reaction was filtered and the filtrate was concentrated in vacuo. The residual oil was purified by HPLC (ethyl acetate-toluene; 2:3) to yield 0.4 g of 3-(8-isoquinolinyl)-2-propyne-1-ol, mp 138°-139° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe cooled reaction
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residual oil was purified by HPLC (ethyl acetate-toluene; 2:3)

Sources & evidence

ORD record
ord-4313f9a52a7f4fc886f0f76d0d4adba6
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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