Triethylamine → 2-(Propargyloxy)ethyl 5-chloroquinolin-8-oxyacetate

HRID 1769262Notes

Reaction equation

HRID 1769262 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:17]([O:20][CH2:21][CH2:22]O)[C:18]#[CH:19].C(N(CC)CC)C>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16][CH2:22][CH2:21][O:20][CH2:17][C:18]#[CH:19])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775962-PropynoxyethanolHCID 15257197Cloquintocet

Product 1

HCID 189476402-(Propargyloxy)ethyl 5-chloroquinolin-8-oxyacetateYield 16.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

5.0 g (0.021 mol) of 5-chloroquinolin-8-oxyacetic acid are heated at 70° C. in 70 ml of thionyl chloride for one hour. The excess thionyl chloride is then distilled off in vacuo and the residue is suspended in 150 ml of carbon tetrachloride. 2.10 g (0.021 mol) of 2-propargyloxyethanol are added dropwise to this suspension, 2.30 g (0.023 mol) of triethylamine are then added dropwise and the mixture is heated under reflux for 12 hours. The suspension is then washed with in each case 70 ml of 2N HCl and 5 percent strength sodium hydroxide solution, the organic phase is dried over magnesium sulfate and the solvent is stripped off in vacuo. The residue is recrystallized from n-heptane. 1.1 g (16.3% of theory) of 2-(propargyloxy)ethyl 5-chloroquinolin-8-oxyacetate of melting point 53° C. are thus obtained.

Workup

  1. distillationThe excess thionyl chloride is then distilled off in vacuo
  2. additionare then added dropwise
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 12 hours
  5. washThe suspension is then washed with in each case 70 ml of 2N HCl and 5 percent strength sodium hydroxide solution
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. customThe residue is recrystallized from n-heptane

Sources & evidence

ORD record
ord-473df83f70ce4276a069e3d7dbb0dbdf
Source dataset
uspto-grants-1995_01
Patent number
US05380852

Reaction notes

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