HCID 14976555, compound → HCID 54192854, compound

HRID 862388Notes

Reaction equation

HRID 862388 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:22])[CH2:20][OH:21]>N1C=CC=CC=1>[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])=[CH:17][CH:18]=1)(=[O:21])[CH2:19][OH:22]

Participants

4

Reactant 2

HCID 14976555HCID 14976555, compoundHCID 53720474HCID 53720474, compound

Product 1

HCID 54192854HCID 54192854, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-(4-hydroxybenzylidene)-7-azaoxindole (2,383 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-333f7c9c4677407ca6082f5ef049bc6f
Source dataset
uspto-grants-1998_02
Patent number
US05719135

Reaction notes

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