1-Methyl-2,3-dihydro-1H-indole → 1-Methylindole

HRID 28418

Reaktionsgleichung

Reaktionsgleichung von HRID 28418
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Komponenten

4

Edukt 1

HCID 558301-Methyl-2,3-dihydro-1H-indole

Produkt 1

HCID 117811-MethylindoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The N-methyl indoline product in Example 47 (70 mg, 0.22 mmol) was dissolved in toluene (9 mL) in a 50-mL flask under N2 fitted with a condenser. MnO2 (199 mg, 2.3 mmol) was added, and the mixture was heated to reflux for 1.5 h. The mixture was cooled to rt, Celite, and the pad was washed several times with liberal amounts of MeOH. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane) to provide the N-methyl indole product (39 mg, 57%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ6.93-7.11 (m, 5H), 6.72 (d, J=8.5 Hz, 1H), 6.42 (d, J=3.1 Hz, 1H), 4.29 (t, J=5.8 Hz, 1H), 3.84-3.96 (m, 2H), 3.77 (s, 3H), 2.99 (dd, J=11.3, 5.0 Hz, 1H), 2.67 (dd, J=11.3, 6.7 Hz, 1H), 2.49 (s, 3H); ESI MS m/z=313 [C19H18F2N2+H]+.

Aufarbeitung

  1. customfitted with a condenser
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1.5 h
  4. washCelite, and the pad was washed several times with liberal amounts of MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f635dd3dc3a84de7a8b31f43f1b13b62
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419985B2

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