Aniline → 3-nitro-N-phenylpyridin-2-amine

HRID 242796ノート

反応式

HRID 242796 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([NH2:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC)CC>CN1C(=O)CCC1>[N+:8]([C:7]1[C:2]([NH:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

参加物

5

反応物 3

HCID 6115Aniline2 回HCID 8471Triethylamine2 回HCID 796132-Chloro-3-nitropyridine

生成物 1

HCID 6117993-nitro-N-phenylpyridin-2-amine収率 58%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-3-nitropyridine (3.49 g, 22.0 mmol), phenylamine (2 mL, 22.0 mmol) and Et3N (3.1 mL, 22.0 mmol) in NMP (7 mL) was stirred at 100° C. for 1.5 h under a nitrogen atmosphere. Additional amounts of Et3N (0.2 mL) and of phenylamine (0.1 mL) were added and the stirring was continued for further 30 min. The mixture was then partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane) affording (3-Nitropyridin-2-yl)phenylamine as a red crystalline solid (2.49 g, 58%). LCMS: RT 3.53 min [M+H]+ 216.0.

後処理

  1. waitthe stirring was continued for further 30 min
  2. customThe mixture was then partitioned between EtOAc and water
  3. extractionThe aqueous phase was further extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane)

出典と根拠

ORDレコード
ord-3ce6f692e56646fc933a88d059878842
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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