Methanesulfonyl chloride → 5-Mesylamino-3-(quinol-4-ylmethylene)-2-oxindole

HRID 356992Notes

Reaction equation

HRID 356992 reaction equation
[NH2:1][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.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>N1C=CC=CC=1>[S:23]([NH: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)([CH3:26])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

Product 1

HCID 676153715-Mesylamino-3-(quinol-4-ylmethylene)-2-oxindoleYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-amino-3-(quinol-4-ylmethylene)-2-oxindole (2.873 g, 10 mmol) in pyridine (10 ml) was added gradually mesylchloride (1.146 g, 10 mmol) at 0°-5° C. under cooling. The reaction mixture was stirred for about 5 h at 0°-5° C. and then for 15 hours 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 70% yield.

Workup

  1. temperatureunder cooling
  2. waitfor 15 hours 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-ec00d732ae1f4797a0ea72a0b1697788
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Reaction notes

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