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

HRID 2362964Notes

Reaction equation

HRID 2362964 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-d752ceddbebb426f8b3bbc4d923bf82d
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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