N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine → N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine

HRID 2272703노트

반응식

HRID 2272703 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[F:18]>[Ni].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[F:18]

참가 물질

4

반응물 1

HCID 86730067N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine

생성물 1

HCID 61466916N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine

시약·촉매·용매 2

HCID 935Nickel촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine (C11) (5.0 g, 19 mmol) and Raney nickel (3 g) in ethyl acetate (400 mL) was degassed three times with hydrogen. The reaction mixture was then hydrogenated at room temperature for 20 hours. After removal of the catalyst via filtration, the filtrate was concentrated in vacuo. Purification via silica gel chromatography afforded the product as a gray solid. Yield: 3.1 g, 13 mmol, 68%. 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J=4.9, 1.6 Hz, 1H), 7.38 (dd, J=11.5, 2.5 Hz, 1H), 7.24 (dd, J=8.5, 8.4 Hz, 1H), 7.06 (dd, J=7.6, 1.6 Hz, 1H), 6.92 (ddd, J=8.7, 2.5, 1.0 Hz, 1H), 6.82 (dd, J=7.6, 4.9 Hz, 1H), 6.37 (br s, 1H), 3.38 (br s, 2H).

후처리

  1. customwas degassed three times with hydrogen
  2. customAfter removal of the catalyst
  3. filtrationvia filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification via silica gel chromatography

출처 및 근거

ORD 기록
ord-5aefc373734747c0880bfe4fe039bffc
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120788B2

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