Ethanol → 2-Amino-4-methoxyphenol

HRID 706228Notes

Reaction equation

HRID 706228 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.C(O)C>[Pd].C(OCC)(=O)C>[NH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 702EthanolHCID 15285Phenol, 4-methoxy-2-nitro-

Product 1

HCID 14191082-Amino-4-methoxyphenolYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxy-2-nitrophenol (30.2 g, 0.18 mol), 10% Pd/C, ethanol (200 mL), and ethyl acetate (200 mL) was hydrogenated at ambient pressure and temperature for three days before it was filtered and concentrated in vacuo to give the title compound as a dark brown solid (20.78 g): 1H NMR (CDCl3, 200 MHz): δ=6.64 (m, 1H), 6.32 (m, 1H), 6.21 (m, 1H), 3.71 (s, 3H).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6685df2402e4010830fe4c4be8e077b
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

Loading…