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

HRID 242796노트

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HRID 242796 반응식
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]

참가 물질

5

반응물 3

HCID 6115Aniline2회HCID 8471Triethylamine2회HCID 796132-Chloro-3-nitropyridine

생성물 1

HCID 6117993-nitro-N-phenylpyridin-2-amine수율 58%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ce6f692e56646fc933a88d059878842
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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