Allyl bromide → HCID 20185127, compound

HRID 2309386Notes

Reaction equation

HRID 2309386 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:13])[CH3:2].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][CH:15]1[O:12][C:8]2=[CH:7][C:6]3[CH2:5][C:4](=[O:13])[N:3]([CH2:1][CH3:2])[C:11]=3[CH:10]=[C:9]2[CH2:16]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 118052822H-Indol-2-one, 1-ethyl-1,3-dihydro-5-hydroxy-

Product 1

HCID 20185127HCID 20185127, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 17.7 g. (0.1 mole) of 1-ethyl-5-hydroxyoxindole, 8.66 ml. (0.1 mole) of allyl bromide and 13.8 g. (0.1 mole) of potassium carbonate in 500 ml. of acetone was heated at reflux for 3 hours. The reaction was cooled, filtered and concentrated. The residue was purified by chromatographing on 550 g. of silica gel using diethyl ether-hexane (1:1, v:v) as the eluent to give 9.8 g. (45% yield) of the desired compound.

Workup

  1. additionA mixture of 17.7 g
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatographing on 550 g
  7. customto give 9.8 g

Sources & evidence

ORD record
ord-c902d569fec24a18b39b5c8e26a8f7ca
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

Loading…