2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 8-nitroquinoxalin-2(1H)-one
Reaction equation
C[Si](C)(C)[CH2:3][CH2:4][O:5]CCl.[N+:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[N:15]=CC(=O)[NH:18]2)([O-:12])=[O:11]>O1CCCC1>[N+:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[NH:15][C:4](=[O:5])[CH:3]=[N:18]2)([O-:12])=[O:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Chloromethyl 2-(trimethylsilyl)ethyl ether (10.0 mL, 56.3 mmol) was added to tetrahydrofuran solution (500 mL) containing a mixture (21.6 g) of the 5-nitroquinoxalin-2-one derivative and the 8-nitroquinoxalin-2-one derivative obtained in the above (1), and then sodium hydride (2.30 g, 60% dispersion in oil, 57.3 mmol) was added thereto under ice-cooling. After the resulting reaction solution was stirred at room temperature for 1.5 hours, aqueous ammonium chloride solution was added thereto, and the mixture was extracted with chloroform. After the organic layer was washed with saturated brine, it was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. To the resulting residue was added 4N hydrogen chloride/1,4-dioxane solution (100 mL), and the solution was stirred at room temperature for 1 hour. After removal of the insolubles by filtration, the filtrate was concentrated in vacuo. The resulting residue was purified by a column chromatography on silica gel to obtain the above 5-nitroquinoxaline-2-one derivative (11.6 g) protected with SEM, as a yellow solid.
Sources & evidence
- ORD record
- ord-f0981b475bb64dbfab0ad6e903d7bd38
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07388010B2
Reaction notes
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