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

HRID 2272703ノート

反応式

HRID 2272703 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5aefc373734747c0880bfe4fe039bffc
出典データセット
uspto-grants-2015_09
特許番号
US09120788B2

反応ノート

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