5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one oxime → 5,7-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine
Reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[N:13]O>N.[Ni]>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[NH2:13]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine: A catalytic amount of Raney nickel (slurry in water) was washed with dry MeOH under argon in a round bottom flask. To a solution of the washed Raney Ni in methanolic ammonia (25 mL, 7N), was added 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one oxime (example 166b) (420 mg, 2.22 mmol), and the mixture was stirred under a balloon of H2 for 20 hr. Upon completion, the reaction was filtered through celite, the filtrate was concentrated in vacuo, diluted with EtOAC, washed with water and brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford 360 mg of 5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine (93%). 1H NMR (500 MHz, CDCl3): δ 1.66-1.83 (m, 4H), 1.96 (m, 2H), 2.19 (s, 3H), 2.28 (s, 3H), 2.55 (m, 1H), 2.66 (m, 1H), 3.97 (m, H), 6.88 (s, 1H), 7.09 (s, 1H).
Workup
- wash5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine: A catalytic amount of Raney nickel (slurry in water) was washed with dry MeOH under argon in a round bottom flask
- filtrationUpon completion, the reaction was filtered through celite
- concentrationthe filtrate was concentrated in vacuo
- additiondiluted with EtOAC
- washwashed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-ede7262c8d0f43c88e7bfa3acc4bbf36
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07476399B2
Reaction notes
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