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

HRID 7090

反応式

HRID 7090 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 105127972-Amino-6-phenyl-nitrobenzene収率 27.1%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 6228Dimethylformamide溶媒2 回

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).

後処理

  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)

出典と根拠

ORDレコード
ord-754b34941ad244829017dcc78f4df6f3
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

関連ノート

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