3-Butyn-1-OL → 4-(3-Quinolinyl)-3-butyn-1-ol

HRID 53639Notes

Reaction equation

HRID 53639 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15]>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>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([C:15]#[C:14][CH2:13][CH2:12][OH:16])[CH:3]=1

Participants

6

Reactant 2

HCID 135663-Butyn-1-OLHCID 214133-Bromoquinoline

Product 1

HCID 106317924-(3-Quinolinyl)-3-butyn-1-olYield 136.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-bromoquinoline (13.57 mL, 0.10 mol) and 3-butyn-1-ol (9.0 mL, 0.12 mol) in 40 mL of triethylamine and 75 mL of dichloromethane is degassed by bubbling in dry nitrogen for 15 minutes, and 0.7 g (0.001 mol) of bis(triphenylphosphine)palladium chloride and 0.013 g of cuprous iodide are added. The flask is flushed with nitrogen and the mixture is heated to reflux for 5 hours. The cooled mixture is diluted with dichloromethane and washed with water, dried (sodium sulfate), and concentrated to give 27 g of an oil. The oil is triturated with diethyl ether to give 18.2 g of the title compound as a tan solid; mp 95.7°-96.7° C.

Workup

  1. customby bubbling in dry nitrogen for 15 minutes
  2. customThe flask is flushed with nitrogen
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 5 hours
  5. additionThe cooled mixture is diluted with dichloromethane
  6. washwashed with water
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3a9fdfef213647288069a2c3da8a519c
Source dataset
uspto-grants-1997_04
Patent number
US05620988

Reaction notes

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