Water → HCID 54444698, compound

HRID 1376794Notes

Reaction equation

HRID 1376794 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:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.Cl[CH2:23][CH:24]([OH:27])[CH2:25][OH:26].O>C1(C)C=CC=CC=1>[OH:27][CH:24]([CH2:25][OH:26])[CH2:23][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:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 54272151HCID 54272151, compound

Product 1

HCID 54444698HCID 54444698, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-hydroxy-3-[(7-azaindol-3-yl)methylene]-2-oxindole (2.773 g, 10 mmol) in toluene (100 ml) was added portionwise under nitrogen NaH 80% (0.300 g, 10 mmol). After the salification was complete 3-chloro-1,2-propane-diol (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. additionwas added
  2. temperaturethe mixture heated
  3. temperatureto reflux for 5 h
  4. additionwas added
  5. washthe organic phase washed
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-208aa9162fcf4ed6b3dd17f9ab772d2f
Source dataset
uspto-grants-1997_09
Patent number
US05663346

Reaction notes

Loading…