Water → 2H-Indol-2-one, 1-(3-chloropropyl)-1,3-dihydro-3-methyl-

HRID 1751076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751076
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22].O>C(#N)C>[Cl:22][CH2:21][CH2:20][CH2:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([CH3:1])[C:3]1=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1509233-Methyloxindole

Produkt 1

HCID 580467792H-Indol-2-one, 1-(3-chloropropyl)-1,3-dihydro-3-methyl-Ausbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 3-methylindolin-2-one (1 g, 6.79 mmol, 1 equiv) in acetonitrile, potassium carbonate (1.877 g, 13.58 mmol, 2.5 equiv) followed by 1-bromo-3-chloropropane (2.01 ml, 20.38 mmol, 3 equiv) were added. The reaction was refluxed for 16 h. Upon cooling water was added and the mixture was extracted into ethyl acetate. The organic layer was further washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified using the Biotage flash chromatography system (SNAP 100 g cartridge, Rf=0.5, gradient—2%-20% ethyl acetate in hexanes) to afford the title compound as a yellow oil (230 mg, 15%); 1H NMR (400 MHz, DMSO-d6): δ 1.31 (d, 3H, J=7.6 Hz); 1.99-2.05 (m, 2H); 3.47-3.53 (m, 1H); 3.66 (t, 2H, J=6.4 Hz); 3.74-3.82 (m, 2H); 7.04 (d, 2H; J=7.6 Hz); 7.24-7.27 (m, 1H); 7.3-7.32 (m, 1H); MS for C12H14ClNO m/z 211.06 (M+H)+.

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction was refluxed for 16 h
  3. additionwas added
  4. extractionthe mixture was extracted into ethyl acetate
  5. washThe organic layer was further washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-92d742d7c016498fa79ef20eb6cd9057
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156840B2

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