반응 #6800

반응 방정식

N-methyl indoline

→

N-methyl indole

수율 57.0%

용매

toluene

반응 조건

후처리

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

실험 절차

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]+.

출처