HCID 14976555, compound → HCID 67614656, compound

HRID 356996Notes

Reaction equation

HRID 356996 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.[C:23](Cl)(=[O:26])[CH2:24][OH:25]>N1C=CC=CC=1>[C: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)(=[O:25])[CH2:23][OH:26]

Participants

4

Reactant 2

HCID 14976555HCID 14976555, compoundHCID 54130696HCID 54130696, compound

Product 1

HCID 67614656HCID 67614656, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-hydroxy-3-(quinol-4-ylmethylene)-2-oxindole (2.883 g, 10 mmol) in pyridine (10 ml) was added gradually glycoloyl chloride (0.945 g, 10 mmol) at 0°-5° C. under cooling. The reaction mixture was stirred for about 4 h at 0°-5° C. and then for 15 h at room temperature. The mixture was poured onto an ice-water mixture, the precipitate filtered off, the residue washed thoroughly with water and then chromatographed on silica gel, using CHCl3 --MeOH mixtures as eluant. Thus pure title compound was obtained in about 60% yield.

Workup

  1. temperatureunder cooling
  2. waitfor 15 h at room temperature
  3. filtrationthe precipitate filtered off
  4. washthe residue washed thoroughly with water
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-f8be00ff11944801a103cda1771ae3eb
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Reaction notes

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