反応 #7186

反応方程式

2-nitrobiphenyl

O-methylhydroxylamine hydrochloride

potassium tert-butoxide

→

2-amino-6-phenyl-nitrobenzene

収率 27.1%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   その他The cooling bath was removed
2. 2
   workup.ADDITIONThe reaction mixture was poured into saturated aqueous NH4Cl (50 mL)
3. 3
   抽出the mixture was extracted with CH2Cl2 (4×50 mL)
4. 4
   乾燥The combined organic extracts were dried (Na2SO4)
5. 5
   濃縮concentrated
6. 6
   その他Purification of the crude material by column chromatography on silica gel (4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate)

実験手順

A suspension of 2-nitrobiphenyl (2.061 g, 10.34 mmol) and O-methylhydroxylamine hydrochloride (1.088 g, 13.02 mmol) in DMF (15 mL) was added to a cold (0° C.) solution of potassium tert-butoxide (5.993 g, 53.40 mmol) and copper(I) chloride (0.246 g, 2.48 mmol) in DMF (35 mL). The cooling bath was removed and the resultant slurry was stirred at room temperature for 20 hours. The reaction mixture was poured into saturated aqueous NH4Cl (50 mL) and the mixture was extracted with CH2Cl2 (4×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate) provided 0.600 g (27%) 2-amino-6-phenyl-nitrobenzene as a yellow oil. 1H NMR (CDCl3) □ 4.99 (br s, 2H), 6.70 (dd, 1H, J=7.2, 1.2 Hz), 6.80 (dd, 1H, J=8.4, 1.2 Hz), 7.29–7.41 (m, 6H).

出典