2-(2-Methyl-2-nitropropyl)naphthalene → alpha,alpha-Dimethyl-2-naphthaleneethanamine

HRID 1349438Notes

Reaction equation

HRID 1349438 reaction equation
[CH3:1][C:2]([N+:15]([O-])=O)([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1>[Ni].C(O)C>[CH3:14][C:2]([NH2:15])([CH3:1])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 99646182-(2-Methyl-2-nitropropyl)naphthalene

Product 1

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineYield 60.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel W2 (200 mg) was suspended in ethanol (10 ml), to the suspension was added 2-(2-methyl-2-nitropropyl)naphthalene (134 mg) obtained in Step 5, and hydrogenation was performed at a pressure of 3.5 atom for 12 hr. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The obtained residue was subjected to crystallization from ethyl acetate to give the title compound (70 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was subjected to crystallization from ethyl acetate

Sources & evidence

ORD record
ord-07b27963acc749de823d3fa04bf7a4d8
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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