반응 #318753

반응 방정식

2-amino-6-nitrobenzoic acid

methyl p-toluenesulfonate

triethylamine

→

methyl 2-amino-6-nitrobenzoate

수율 59.4%

용매

DMF

반응 조건

후처리

1. 1
   기타After removing DMF at 60°
2. 2
   workup.DISSOLUTION0.2 mm pressure, the residue was dissolved in ETOAc
3. 3
   세척washed with a saturated solution of NaHCO3
4. 4
   추출The EtOAc extract
5. 5
   건조was dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   세척Flash chromatography over silica gel and elution with 50% toluene-50% CHCl3

실험 절차

A mixture of 2-amino-6-nitrobenzoic acid (11.9 g, 65.3 mmol), methyl p-toluenesulfonate (15.1 g, 81.1 mmol) and triethylamine (6.60 g, 65.3 mmol) in DMF (170 ml) was stirred under N2 at 60° for 18 hours. After removing DMF at 60° and 0.2 mm pressure, the residue was dissolved in ETOAc and washed with a saturated solution of NaHCO3 followed by a saturated aqueous solution of NaCl. The EtOAc extract was dried (Na2SO4), filtered and concentrated under reduced pressure. Flash chromatography over silica gel and elution with 50% toluene-50% CHCl3 gave methyl 2-amino-6-nitrobenzoate (7.6 g, 59.4%), m.p. 105-107°.

출처