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

HRID 6704

Reaktionsgleichung

Reaktionsgleichung von HRID 6704
[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 ref lux 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) δ 6.93-7.11 (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 to ref lux for 1.5 h
  3. washCelite, and the pad was washed several times with liberal amounts of MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0d4e9f47c44c454597841332d2046dc8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084152B2

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