5,7-Dimethyl-6-nitro-3,4-dihydronaphthalen-1(2H)-one → 6-Amino-5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1662282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662282
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([CH3:15])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:16]>CO.[Ni]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:15])[C:7](=[O:16])[CH2:6][CH2:5][CH2:4]2

Komponenten

4

Edukt 1

HCID 598088855,7-Dimethyl-6-nitro-3,4-dihydronaphthalen-1(2H)-one

Produkt 1

HCID 552716636-Amino-5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5,7-dimethyl-6-nitro-3,4-dihydronaphthalen-1(2H)-one (1 g, 4.56 mmol) in 50 ml of methanol was added a catalytic amount of Raney Ni. The mixture was hydrogenated under regular pressure at room temperature for 4 hours and filtered through Celite and washed with methanol. The filtrate was evaporated to dryness under reduced pressure and dried in vacuo to give the crude product, which is pure enough for next step. 1H-NMR δ (CDCl3, 300 MHz): 7.77 (s, 1H), 4.09 (brs, 2H, exchangeable with D2O), 2.85 (t, J=6.0 Hz, 2H), 2.54 (t, J=6.0 Hz, 2H), 2.19 (s, 3H), 2.09 (s, 3H), 2.10 (m, 2H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97c39130ae73447cba62463ae992c281
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030518B2

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