反应 #6800

反应方程式

N-methyl indoline

→

N-methyl indole

收率 57.0%

溶剂

toluene

反应条件

后处理

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

实验过程

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]+.

来源