تفاعل #7186

معادلة التفاعل

2-nitrobiphenyl

O-methylhydroxylamine hydrochloride

potassium tert-butoxide

→

2-amino-6-phenyl-nitrobenzene

المردود 27.1%

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooling bath was removed
2. 2
   workup.ADDITIONThe reaction mixture was poured into saturated aqueous NH4Cl (50 mL)
3. 3
   استخلاصthe mixture was extracted with CH2Cl2 (4×50 mL)
4. 4
   تجفيفThe combined organic extracts were dried (Na2SO4)
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification of the crude material by column chromatography on silica gel (4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate)

الإجراء التجريبي

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).

المصدر