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

HRID 1662282Notes

Reaction equation

HRID 1662282 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-97c39130ae73447cba62463ae992c281
Source dataset
uspto-grants-2011_10
Patent number
US08030518B2

Reaction notes

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