Water → 5-methoxy-4,7-dimethyl-2,3-dihydro-1H-indol-2-one

HRID 985594Notes

Reaction equation

HRID 985594 reaction equation
[CH3:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH3:13])=[C:7]2[C:3]=1[CH:4](SC)[C:5](=[O:14])[NH:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.O>ClCCl>[CH3:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH3:13])=[C:7]2[C:3]=1[CH2:4][C:5](=[O:14])[NH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 225068774,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 225068425-methoxy-4,7-dimethyl-2,3-dihydro-1H-indol-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,7-dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indol-2-one (17.8 g, 75 mmol) in dichloromethane (350 ml) were added triphenylphosphine (23.6 g, 90 mmol) and toluenesulfonic acid monohydrate (17.1 g, 90 mmol) at room temperature and stirred for 3 hours. The reaction mixture was poured into a cold water, and the precipitated crystals were collected by filtration. After washing with dichloromethane and water, 12.4 g of the title compound was obtained.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washAfter washing with dichloromethane and water

Sources & evidence

ORD record
ord-72f7bf7f0b5b4251afec49cb701fb7c1
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

Loading…