تفاعل #2446148

معادلة التفاعل

N-(2-amino-4-bromophenyl)-2-chloroacetamide

sodium iodide

sodium carbonate

→

6-bromo-3,4-dihydroquinoxalin-2(1H)-one

المردود 34.1%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas refluxed overnight under an atmosphere of nitrogen
2. 2
   أخرىThen the acetonitrile was removed under vacuum
3. 3
   استخلاصExtraction with ethyl acetate
4. 4
   غسيلwashing of the combined organic layers with brine
5. 5
   تجفيفdrying over MgSO4
6. 6
   أخرىremoving the solvent
7. 7
   أخرىunder reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1)

الإجراء التجريبي

A mixture of N-(2-amino-4-bromophenyl)-2-chloroacetamide (4.5 g, 17.0 mmol), sodium iodide (101 mg, 2.0 mmol) and sodium carbonate (3.6 g, 33.8 mmol) in 300 ml acetonitrile was refluxed overnight under an atmosphere of nitrogen. Then the acetonitrile was removed under vacuum. The resulting solid was suspended in 150 ml water acidified to pH 5-6 with 1 N HCl. Extraction with ethyl acetate, washing of the combined organic layers with brine, drying over MgSO4, removing the solvent under reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1) yielded 6-bromo-3,4-dihydroquinoxalin-2(1H)-one (1.3 g, 5.8 mmol, 34%) as yellow solid.

المصدر