Aniline → (2-Nitropyridin-3-yl)phenylamine

HRID 242970

反応式

HRID 242970 の反応式
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

参加物

5

反応物 3

HCID 6115AnilineHCID 8471TriethylamineHCID 27628023-Fluoro-2-nitropyridine

生成物 1

HCID 20184004(2-Nitropyridin-3-yl)phenylamine収率 154.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-fluoro-2-nitropyridine (1.07 g, 6.75 mmol), aniline (1.8 mL, 20.2 mmol) and Et3N (2.8 mL, 20.2 mmol) in DMF (10 mL) was stirred at 100° C. for 16 h under a nitrogen atmosphere. After cooling to RT, the volatiles were removed under reduced pressure. The resulting residue was partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM) to afford the title compound as a red oil (2.24 g, quantitative). LCMS (Method C): RT 3.03 min [M+H]+ 216.2.

後処理

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under reduced pressure
  3. customThe resulting residue was partitioned between DCM and water
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM)

出典と根拠

ORDレコード
ord-8f761dc54c3a4619aa346344671b6aeb
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

関連ノート

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