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

HRID 1664300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664300
[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

Komponenten

6

Edukt 1

HCID 521800N-benzyl-2-nitroaniline

Produkt 1

HCID 2735482N1-Benzylbenzene-1,2-diamineAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidKatalysatorHCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-19fd943a28b8423eab6ec308b1a571c8
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039467B2

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