1-(Benzyloxy)-2,3-dinitrobenzene → 3-(Benzyloxy)benzene-1,2-diamine

HRID 1650671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650671
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[N+:18]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 139713581-(Benzyloxy)-2,3-dinitrobenzeneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 44012883-(Benzyloxy)benzene-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of O-benzyl-2,3-dinitrophenol (Description 12) (4.5 g) in ethanol (300 ml) was hydrogenated at atmospheric pressure over Raney nickel (2 g) until uptake of hydrogen ceased. The solution was filtered and evaporated to dryness in vacuo to afford unstable O-benzyl-2,3-diaminophenol which was immediately heated with phenylacetic acid (20 g) at 140°-150° C. for 3 h. The product was heated under reflux with 5N-hydrochloric acid (70 ml) for 3 h and neutralised with 10% sodium carbonate. The mixture was extracted with chloroform, and the organic layer washed with 10% sodium carbonate, water and dried (Na2SO4). The recovered product was chromatographed on Silica Gel 60 (250 g) eluting with ethylacetate-chloroform (1:19) to afford the title compound (1.6 g), m.p. 172°-174° C. (ethanol/ether).

Aufarbeitung

  1. filtrationThe solution was filtered
  2. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-59d1cbcfd74041f0b552ef46e15ed389
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925853

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