2-Nitrobiphenyl → 2-Amino-6-phenyl-nitrobenzene

HRID 7090

반응식

HRID 7090 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].Cl.CO[NH2:19].CC(C)([O-])C.[K+]>CN(C=O)C.[Cu]Cl>[NH2:19][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]=1[N+:1]([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 68292-NitrobiphenylHCID 521874O-Methylhydroxylamine hydrochlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 105127972-Amino-6-phenyl-nitrobenzene수율 27.1%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was poured into saturated aqueous NH4Cl (50 mL)
  3. extractionthe mixture was extracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-754b34941ad244829017dcc78f4df6f3
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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