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

HRID 1664300노트

반응식

HRID 1664300 반응식
[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

참가 물질

6

반응물 1

HCID 521800N-benzyl-2-nitroaniline

생성물 1

HCID 2735482N1-Benzylbenzene-1,2-diamine수율 57.1%

시약·촉매·용매 4

HCID 313Hydrochloric Acid촉매HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-19fd943a28b8423eab6ec308b1a571c8
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039467B2

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