5-Ethyl-2-nitrophenol → 2-Amino-5-ethylphenol

HRID 1385412Notes

Reaction equation

HRID 1385412 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][C:5]=1[OH:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][C:5]=1[OH:12]

Participants

4

Reactant 1

HCID 155967145-Ethyl-2-nitrophenol

Product 1

HCID 47121672-Amino-5-ethylphenolYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-5-ethylphenol (1 g, 6.4 mmol) in methanol (250 mL) was added 10% Pd/C (100 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5%MeOH/CH2CH2) gave the desired product (750 mg, 91 %). 1H NMR (CD3OD): d 6.41-6.17 (m, 3H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-31412d0e41c040fcbc647c8d18e81720
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

Loading…