1-(2-Hydroxy-3-nitrophenyl)-ethanone → 3-Amino-2-hydroxyacetophenone

HRID 325726Notes

Reaction equation

HRID 325726 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[OH:13])=[O:3]>C(O)C.[Pt]>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[OH:13])=[O:3]

Participants

4

Reactant 1

HCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

Product 1

HCID 4592943-Amino-2-hydroxyacetophenone

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-hydroxy-3-nitroacetophenone [4.0 g; prepared by the method of Allen et al., J. Chem. Soc., (1949), 821] in ethanol (150 ml) was hydrogenated at 25° C. and 50 p.s.i. for 2.5 hours, using a catalyst of platinum on charcoal. The mixture was filtered and the filtrate was evaporated in vacuo to give a black solid, which was purified by chromatography on a column of silica gel, using diethyl ether as eluant. The fastest moving band (yellow) was collected to give 3-amino-2-hydroxyacetophenone (3.0 g), in the form of a bright yellow solid, m.p. 95°-97° C.

Workup

  1. customprepared by the method of Allen et al., J
  2. customwas hydrogenated at 25° C.
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customto give a black solid, which
  6. customwas purified by chromatography on a column of silica gel
  7. customwas collected

Sources & evidence

ORD record
ord-6e1246759c8e40a4a9620a08b5184f21
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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