Ethanol → 3-Amino-4-hydroxybenzonitrile

HRID 1944695Notes

Reaction equation

HRID 1944695 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O.CCO>[Pd].C(OCC)(=O)C>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxy-3-nitrobenzonitrile (100 mg, 0.61 mmol), palladium on charcoal (10 mg, 10%), EtOH (0.67 mL) and ethyl acetate (0.33 mL) was hydrogenated at rt for 2 h. Then the mixture was filtered and concentrated to give 3-amino-4-hydroxybenzonitrile 60 mg (73%) as a solid.

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ebdd0ca8865243f088b3624170075b5e
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

Loading…