ChemicalBook CAS DataBase List N-METHYLISATIN

N-METHYLISATIN synthesis

10synthesis methods

Product Name:N-METHYLISATIN
CAS Number:2058-74-4
Molecular formula:C9H7NO2
Molecular Weight:161.16

74-83-9
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91-56-5 Synthesis

91-56-5
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2058-74-4
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$12.00/1mg

Yield:2058-74-4 86%

Reaction Conditions:

Stage #1:indole-2,3-dione with potassium carbonate in N,N-dimethyl-formamide at 20; for 2 h;Cooling with ice;
Stage #2:methyl bromide in N,N-dimethyl-formamide at 60;Cooling with ice;

Steps:

General method for alkylation of isatin
General procedure: The isatin 1 (1 equv.) was taken in anhyd DMF (2 mL per 0.1 mmol of isatin) and cooled on ice bath with stirring. Solid K2CO3 (1.2 equv.) was added in one portion and the dark coloured suspension was stirred at room temp for 2 h. The appropriate alkyl bromide (1.2 equv.) was added and reaction mixture was stirred at 60 °C for 8-12 h until isatin starting material was consumed (monitoredby TLC). The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 50 mL). The combined organic extract was washed with brine (2 50 mL), and dried overanhyd Na2SO4 and filtered. The solvent was evaporated and thecrude product was purified by using silica gel column chromatography(EtOAc: hexanes). This procedure is utilized in the preparationof 3a and 3b.

References:

Majik, Mahesh S.;Rodrigues, Cheryl;Mascarenhas, Stacey;D'Souza, Lisette [Bioorganic Chemistry,2014,vol. 54,p. 89 - 95]

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