Water → HCID 54475812, compound

HRID 356995Notes

Reaction equation

HRID 356995 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.Cl[CH2:24][CH:25]([OH:28])[CH2:26][OH:27].O>C1(C)C=CC=CC=1>[OH:28][CH:25]([CH2:26][OH:27])[CH2:24][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 54130696HCID 54130696, compound

Product 1

HCID 54475812HCID 54475812, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-hydroxy-3-(quinol-4-ylmethylene)-2-oxindole (2.883 g, 10 mmol) in toluene (100 ml) was added portionwise under nitrogen NaH 80% (0.300 g, 10 mmol). After salification was complete, 3-chloro-1,2-propanediol (1.547 g, 14 mmol) was added and the mixture heated to reflux for 5 h. After cooling, water was added, the organic phase washed and evaporated to dryness. The residue was submitted to flash chromatography, using CHCl3 --MeOH mixtures as eluant to give pure title compound in about 70% yield.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. washthe organic phase washed
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-64af8621fca74abf971272230bba2100
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Reaction notes

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