N-Benzyl-N,2-dimethyl-5-nitro-aniline → HCID 55091508, Verbindung

HRID 2061440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061440
[CH2:1]([N:8]([CH3:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.Cl>[CH2:1]([N:8]([CH3:19])[C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 66915963N-Benzyl-N,2-dimethyl-5-nitro-aniline

Produkt 1

HCID 55091508HCID 55091508, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

SnCl2-dihydrate (1117 mg, 4.95 mmol) is added to a solution of N-Benzyl-N,2-dimethyl-5-nitro-aniline (247 mg, 0.96 mmol) in methanol (10 mL) and conc. HCl (1 mL). After boiling under reflux for 2.5 h, volatiles are evaporated under reduced pressure and the residue is partitioned between EtOAc and water, the pH being adjusted to approx. 10 by the addition of 2N NaOH. The organic layer is washed with sat. brine, dried (Na2SO4), and evaporated. Chromatography of the residue (silica gel, hexanes/EtOAc 3:2) yields N3-benzyl-N3,4-dimethyl-benzene-1,3-diamine.

Aufarbeitung

  1. temperatureunder reflux for 2.5 h
  2. customvolatiles are evaporated under reduced pressure
  3. customthe residue is partitioned between EtOAc and water
  4. additionby the addition of 2N NaOH
  5. washThe organic layer is washed with sat. brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-08d945441edc49bbbab1c9577b101778
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283356B2

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