1-Bromo-3-chloropropane → 1-(3-Chloropropyl)indolin-2-one

HRID 1751037Notes

Reaction equation

HRID 1751037 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:15][CH2:14][CH2:13][CH2:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 321710Oxindole

Product 1

HCID 180699061-(3-Chloropropyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Oxindole (2.00 g, 0.0150 mol), 1-bromo-3-chloropropane (2.97 mL, 0.03 mol), and potassium carbonate (4.15 g, 0.03 mol) in acetonitrile (40 mL) were heated at reflux for 20 hours. The mixture was evaporated, diluted with ethyl acetate, washed with 2M aqueous hydrochloric acid and brine, dried (MgSO4), and evaporated. The residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes) to give product as an oil which solidified on standing (1.57 g, 50%); MS for C11H12ClNO m/z 210 (M+H)+.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe mixture was evaporated
  3. additiondiluted with ethyl acetate
  4. washwashed with 2M aqueous hydrochloric acid and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes)
  8. customto give product as an oil which

Sources & evidence

ORD record
ord-6b3a8dd9ca414553ad553e3ccb4c6562
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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