4-methoxy-N-(4-nitrophenyl)aniline → HCID 10243439、化合物

HRID 1879547ノート

反応式

HRID 1879547 の反応式
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>CC(O)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:17]=2[CH:18]=1)=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3

参加物

4

反応物 1

HCID 27480234-methoxy-N-(4-nitrophenyl)aniline

生成物 1

HCID 10243439HCID 10243439、化合物収率 64%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To 4-methoxy-N-(4-nitrophenyl)aniline (785 mg, 3.2 mmol) in 5 mL of AcOH was added Pd(OAc)2 (1.43 g, 6.4 mmol). The mixture was heated at 100° C. for 15 h under air atmosphere and cooled to rt and concentrated under reduced pressure. The residue was taken up in EtOAc (100 mL) and washed with NaHCO3 (2×100 mL) and water (100 mL). After solvent removal, the crude was purified with chromatography (hexane/EtOAc) to afford 3-methoxy-6-nitro-9H-carbazole as a orange solid (495 mg, 64%). 1H NMR (400 MHz, acetone-d6) δ 10.90 (s, 1H), 9.09 (d, J=2.4 Hz, 1H), 8.27 (dd, J=9.2, 2.4 Hz, 1H), 7.96 (d, J=2.4 Hz, 1H), 7.62 (d, J=9.2 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.14 (dd, J=8.8, 2.8 Hz, 1H), 3.92 (s, 3H); MS (ESI) m/z 243 (M+H+).

後処理

  1. temperaturecooled to rt
  2. concentrationconcentrated under reduced pressure
  3. washwashed with NaHCO3 (2×100 mL) and water (100 mL)
  4. customAfter solvent removal
  5. customthe crude was purified with chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-98ba58cf53cc42438a2cf6c904477f80
出典データセット
uspto-grants-2012_11
特許番号
US08318132B2

反応ノート

読み込み中…