m-Nitroacetophenone → 1-(3-Aminophenyl)ethanol

HRID 2398190Notes

Reaction equation

HRID 2398190 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>[Ni].O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]([OH:12])[CH3:11]

Participants

5

Reactant 2

HCID 8494m-NitroacetophenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 2224611-(3-Aminophenyl)ethanolYield 38.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Following the procedure of Example I m-nitroacetophenone (82.5 g., 0.50 mole; 99% purity by GLC), water (300 ml.), and Raney nickel catalyst (27 g. (wet), Grace No. 4200) charged to a 1 liter Parr stirring autoclave. The hydrogen pressure was 50 psi initially and allowed to decrease to 40 psi whereupon the pressure was raised to 50 psi and again allowed to decrease as hydrogenation continued. The temperature was slowly raised from 25° C to 100° C. After 61/2 hours, hydrogen absorption apparently ceased. Work-up as in example I gave 26.5 g. m-amino-α-methylbenzyl alcohol (38.7% yield) which was 100% pure by GLC and a residue of 38.1 g. which contained 87.2% m-amino-α-methylbenzyl alcohol and 12.8% m-aminoacetophenone.

Workup

  1. additioncharged to a 1 liter Parr
  2. temperaturewas raised to 50 psi
  3. temperatureThe temperature was slowly raised from 25° C to 100° C
  4. customAfter 61/2 hours, hydrogen absorption
  5. customgave 26.5 g

Sources & evidence

ORD record
ord-5c66a94ee57b4c7cbef3e90d0737d51b
Source dataset
uspto-grants-1977_05
Patent number
US04024187

Reaction notes

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