Hydrazine hydrate (1:1) → 3-Amino-4-hydroxybenzonitrile

HRID 1968948Notes

Reaction equation

HRID 1968948 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.O.NN>C(O)C.CO.[Ni]>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[C:6]#[N:7]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 49%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

4-Hydroxy-3-nitrobenzonitrile (0.5 g, 3.05 mmol) was dissolved in ethanol (20 mL) and methanol (10 mL), and Raney-Nickel (1 mL, 10% aqueous solution) was added at rt followed by hydrazine mono hydrate (0.296 mL, 6.09 mmol). The mixture was stirred at rt overnight. The mixture was then filtered through celite and concentrated by rotary evaporation. The residue was purified via chromatography (silica, n-hexane to ethyl acetate) to give 3-amino-4-hydroxybenzonitrile (D19, 200 mg, 49%) as an orange solid.

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated by rotary evaporation
  3. customThe residue was purified via chromatography (silica, n-hexane to ethyl acetate)

Sources & evidence

ORD record
ord-f36ab4f335684d0a8391ad6bfa450794
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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