4-(2-Bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one → 2H-Indol-2-one, 4-(2-bromoethyl)-1,3-dihydro-

HRID 358822Notes

Reaction equation

HRID 358822 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6](Cl)[C:7](=[O:13])[NH:8]2.O.[PH2]([O-])=O.[Na+]>[Pd].O>[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2

Participants

5

Reactant 2

HCID 103560034-(2-Bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-oneHCID 178418950HCID 178418950, compound

Product 1

HCID 99918542H-Indol-2-one, 4-(2-bromoethyl)-1,3-dihydro-Yield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

4-(2'-Bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one (23.6 g. 86 mmol), sodium hypophosphite hydrate (35 g) and 10% palladium/carbon (60% w/w wet, 2.6 g) were stirred in industrial methylated spirit (250 ml)/water (30 ml) at 80° C. The reaction was complete after 2 hours as monitored by HPLC. Inorganic components were removed by filtration and the organic solvent was removed in vaccuo. The solid residue was slurried in water (100 ml) and dried overnight to give 17.0 g (82%) of 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one.

Workup

  1. customInorganic components were removed by filtration
  2. customthe organic solvent was removed in vaccuo
  3. customdried overnight

Sources & evidence

ORD record
ord-2813a718cc3647a98d0efbd87921e660
Source dataset
uspto-grants-1991_03
Patent number
US04997954

Reaction notes

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