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

HRID 2398189Notes

Reaction equation

HRID 2398189 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 53%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
26 °C

Procedure

m-Nitroacetophenone [123.8 g., 0.75 mole, 99% purity by gas-liquid chromatography (GLC)], water (450 ml.) and Raney nickel catalyst (40 g. (wet) Grace No. 4200) was charged to a 1 liter Parr stirring autoclave. The reaction mass was stirred at 100 psi constant hydrogen pressure while the temperature was adjusted slowly to 99° C (the exotherm of hydrogenation contributed initially to the temperature increase from ambient, 26° C). After 4 hours there was no further evidence of hydrogen absorption. The hydrogenate was filtered at 60°-70° C and the clear, light amber colored filtrate was cooled to 10° C with stirring. After stirring one hour, the original filtrate was again filtered to give 54.5 g. of m-amino-α-methylbenzyl alcohol (53.0% yield) which was 100% pure by GLC. The filtrate was evaporated under vacuum to leave a residue of 42.1 g. which was 100% m-amino-α-methylbenzyl alcohol by GLC. Total yield of 96.6 g. (94.0% yield).

Workup

  1. customwas adjusted slowly to 99° C
  2. customno further evidence of hydrogen absorption
  3. filtrationThe hydrogenate was filtered at 60°-70° C
  4. temperaturethe clear, light amber colored filtrate was cooled to 10° C
  5. stirringwith stirring
  6. stirringAfter stirring one hour
  7. filtrationthe original filtrate was again filtered
  8. customto give 54.5 g

Sources & evidence

ORD record
ord-dd7fe59c9f3b45b5a690752716df574f
Source dataset
uspto-grants-1977_05
Patent number
US04024187

Reaction notes

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