Sodium → HCID 18947639, compound

HRID 1769260Notes

Reaction equation

HRID 1769260 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:17](=[N:20][O:21][CH2:22][CH:23](O)[CH3:24])([CH3:19])[CH3:18].[Na]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16][CH:23]([CH3:24])[CH2:22][O:21][N:20]=[C:17]([CH3:19])[CH3:18])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 3

HCID 5360545SodiumHCID 152789382-Propanone, O-(2-hydroxypropyl)oximeHCID 22506560Acetic acid, 2-[(5-chloro-8-quinolinyl)oxy]-, ion(1-)

Product 1

HCID 18947639HCID 18947639, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4.75 g (0.02 mol) of 5-chloroquinolin-8-oxyacetate are suspended in 50 ml of tetrahydrofuran, 3.2 g (0.02 mol) of N,N'-carbonyldiimidazole are added and the suspension is heated to 50° C. until the evolution of gas has ended. A solution of 2.62 g (0.02 mol) of 1-isopropylideneaminooxy-2-propanol and 50 mg of sodium in 10 ml of tetrahydrofuran (THF) is added dropwise to this suspension and the mixture is heated under reflux. After the reaction, the THF is stripped off under reduced pressure, the residue is taken up in ethyl acetate and the solution is washed with 5% strength NaOH and NaCl solution. The organic phase is dried over MgSO4 and concentrated and the residue is recrystallized from heptane. 3.6 g (45.6% of theory) of 1-isopropylideneaminooxy-2-propyl 5-chloroquinolin-8-oxyacetate of melting point 102° C. are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. customAfter the reaction
  4. washthe solution is washed with 5% strength NaOH and NaCl solution
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated
  7. customthe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-ffcdbcb35a364fd8bdd6aafc828853c8
Source dataset
uspto-grants-1995_01
Patent number
US05380852

Reaction notes

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