2-Methyl-5-phenylbenzonitrile → 2-Methyl-5-phenylbenzylamine

HRID 1883637Notes

Reaction equation

HRID 1883637 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].O.N>O1CCOCC1.C(O)C.[Ni].O>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

7

Reactant 2

HCID 111715372-Methyl-5-phenylbenzonitrileHCID 12896473Azane;hydrate

Product 1

HCID 235082132-Methyl-5-phenylbenzylamineYield 82.6%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.0 g (5.17 mmol) of 2-methyl-5-phenylbenzonitrile (produced in the same manner as in the above-mentioned Reference Production Example 1 (2)) was dissolved in a mixed solvent of 8 ml of 1,4-dioxane and 8 ml of ethanol, and to this solution was added 1.0 g of a suspension of 2 ml of 28 wt % ammonia water and Raney nickel W2 (manufactured by Aldrich; 50 wt % in water). This mixture was stirred for 8 hours at room temperature under hydrogen atmosphere, then, filtrated through celite, and the celite was washed with ethanol and water. The filtrate and washed solution was combined and concentrated under reduced pressure, and the residue was distilled by using Kugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.), to obtain 842 mg (4.27 mmol) of 2-methyl-5-phenylbenzylamine.

Workup

  1. filtrationfiltrated through celite
  2. washthe celite was washed with ethanol and water
  3. washThe filtrate and washed solution
  4. concentrationconcentrated under reduced pressure
  5. distillationthe residue was distilled
  6. distillationKugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.)

Sources & evidence

ORD record
ord-9b56c1dae3c44bddac9e06defce4dde5
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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