N-benzyl-2-nitroaniline → N1-Benzylbenzene-1,2-diamine

HRID 1869231ノート

反応式

HRID 1869231 の反応式
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.Cl.[Fe]>[CH2:1]([NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 1

HCID 521800N-benzyl-2-nitroaniline

生成物 1

HCID 2735482N1-Benzylbenzene-1,2-diamine収率 57.1%

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid触媒HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of benzyl-(2-nitro-phenyl)-amine (1068) (2.5 g, 10.43 mmol) in ethanol (150 mL) and water (10 mL) was added iron (8.7 g, 155.7 mmol) followed by 30 drops of concentrated HCl, and the resulting mixture was heated overnight at reflux. The reaction mixture was quenched with water, diluted with DCM and the layers were separated. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to give a brown oily residue. Further purification by column chromatography (SiO2, 20% ethyl acetate/hexanes) afforded N-benzyl-benzene-1,2-diamine (1069) as a dark yellow oil (1.18 g, 57%). 1H NMR (400 MHz, CDCl3) 7.41-7.24 (m, 5H), 6.82-6.67 (m, 4H), 4.32 (s, 2H), 3.56 (b, 3H, NH).

後処理

  1. temperaturethe resulting mixture was heated overnight
  2. temperatureat reflux
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with DCM
  5. customthe layers were separated
  6. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a brown oily residue
  10. customFurther purification by column chromatography (SiO2, 20% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-0b6caa26451443699489910e0965182a
出典データセット
uspto-grants-2009_12
特許番号
US07638513B2

反応ノート

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