1-(Methylsulfonyl)-2-nitrobenzene → 2-Methanesulfonylaniline

HRID 479078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479078
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O)(=[O:4])=[O:3]>C(O)C.[Pd]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])(=[O:3])=[O:4]

Komponenten

4

Edukt 1

HCID 117358061-(Methylsulfonyl)-2-nitrobenzene

Produkt 1

HCID 2446592-MethanesulfonylanilineAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Methylsulfonyinitrobenzene (6.0g, 0.03 mol) was suspended in absolute ethanol (60 mL). 6% Pd/C catalyst (50% wet; 1.01 g) was added and the suspension was hydrogenated in a Parr shaker at 40 psi for 16 hours. The catalyst was then filtered over a pad of infusorial earth and washed with ethanol (2×10 ml). The filtrate was concentrated to dryness on a rotary evaporator. 4.94 g (96% yield) of the product was obtained as white crystals. mp 82-84° C. 1H NMR (CDCl3) δ 7.7 (dd, 1H), 7.2-7.3 (m, 1H), 6.5-6.8 (m, 2H), 5.04 (bs, 2H), 3.07 (s, 3H); CIMS (m/e) 172 (M+H+, 100%).

Aufarbeitung

  1. filtrationThe catalyst was then filtered over a pad of infusorial earth
  2. washwashed with ethanol (2×10 ml)
  3. concentrationThe filtrate was concentrated to dryness on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-1e167dc2903246368c399a989535b790
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642416B2

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