3,3-diMethoxyindolin-2-one synthesis
- Product Name:3,3-diMethoxyindolin-2-one
- CAS Number:66346-69-8
- Molecular formula:C10H11NO3
- Molecular Weight:193.2
Yield:66346-69-8 81%
Reaction Conditions:
with toluene-4-sulfonic acid in methanol at 80;
Steps:
3,3-dimethoxyindolin-2-one:
In a round-bottom flask was added isatin (1 g, 6.8mmol), MeOH (50 mL), pTsOH (360 mg, 1.4 mmol, 20 mol%), and TMOF (4.0mL, 35 mmol, 5.2 equiv.) and the reaction stirred at 80°C in an oil bath, overnight.The reaction was cooled down to room temperature and the MeOH evaporatedunder reduced pressure. The crude product was purified by silica gel flashchromatography using hexane:AcOEt (5:1) and (1:1) as eluents. Thecorresponding 3,3-dimethoxyindolin-2-one (1.15 g, 81% yield) was obtained asan orange oil.1H NMR (CDCl3, 400 MHz) δ: 8.64 (s br, 1H, NH), 7.40-7.39 (d, J= 4 Hz, 1H, Ar),7.32-7.29 (t, 1H, Ar), 7.09-7.05 (t, J= 8 Hz, 1H, Ar), 6.91-6.89 (d, J= 8 Hz, 1H,Ar), 3.57 (s, 6H, OMe).13C APT NMR (CDCl3, 100 MHz) δ: 173.1, 140.6, 130.9, 125.3, 125.1, 122.9,111.1, 97.4, 51.0
References:
Marques, Carolina S.;López, óscar;Leitzbach, Luisa;Fernández-Bola?os, José G.;Stark, Holger;Burke, Anthony J. [Synthesis,2022,vol. 54,# 19,art. no. SS-2021-M0728-OP,p. 4304 - 4319] Location in patent:supporting information
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