Hexane → 4-Amino-3-hydroxybenzonitrile

HRID 357287Notes

Reaction equation

HRID 357287 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].[H][H].CCCCCC.C(OCC)(=O)C>[Pd].C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 151119213-Hydroxy-4-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 101977194-Amino-3-hydroxybenzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A parr bottle was charged with palladium on activated carbon (5%, 0.204 g). A solution of 3-hydroxy-4-nitrobenzonitrile (1.36 g, 0.00829 mol) in 41 ml of ethanol was added. The reaction mixture was placed under 25 psi of hydrogen gas and shaken for 1 hour. TLC (1:1 hexane:ethyl acetate) shows that no starting material remained. The mixture was filtered through Celite® and evaporated to yield 3-hydroxy-4-aminobenzonitrile, 1.08 g (0.00806 mol, 97%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated

Sources & evidence

ORD record
ord-d4310e2f557a481883d6a2051a17e416
Source dataset
uspto-grants-1998_11
Patent number
US05840764

Reaction notes

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