反応 #56696

反応方程式

N-methyl indoline

→

N-methyl indole

収率 57.0%

溶媒

toluene

反応条件

後処理

1. 1
   その他fitted with a condenser
2. 2
   温度the mixture was heated
3. 3
   温度to reflux for 1.5 h
4. 4
   洗浄Celite, and the pad was washed several times with liberal amounts of MeOH
5. 5
   濃縮The filtrate was concentrated in vacuo
6. 6
   その他the residue was purified by silica gel chromatography (gradient 25-35% EtOAc/hexane)

実験手順

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]+.

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