Ammonia → HCID 15461890, compound

HRID 2306155Notes

Reaction equation

HRID 2306155 reaction equation
[OH:1][CH2:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[C:4]#[N:5].N>CO.[Ni]>[OH:1][CH2:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[CH2:4][NH2:5]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 15461889HCID 15461889, compound

Product 1

HCID 15461890HCID 15461890, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

52.4 g (0.3 mol) of 3-hydroxy-2-(2,6-dimethylphenyl)-propionitrile are dissolved in 400 ml methanol and combined with 50 9 of NH3. The reaction mixture is hydrogenated under a pressure of 70 bar and at a reaction temperature of 70° C. in the presence of 60 g Raney nickel. After 4 h the mixture is cooled, filtered over silica gel and the solvent is eliminated in vacuo. The residue is distilled under high vacuum. Yield: 40.6 g (76%), boiling point: 135-140° C. (0.02 mbar); melting point of the hydrochloride: 166° C.

Workup

  1. temperatureAfter 4 h the mixture is cooled
  2. filtrationfiltered over silica gel
  3. distillationThe residue is distilled under high vacuum
  4. custom166° C.

Sources & evidence

ORD record
ord-05d60e1f58e648759ec84d5b844a1d86
Source dataset
uspto-grants-2002_08
Patent number
US06441237B1

Reaction notes

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