2-(4-Hydroxy-3-nitrophenyl)propanenitrile → 2-(3-Amino-4-hydroxyphenyl)propanenitrile

HRID 2082911Notes

Reaction equation

HRID 2082911 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]([CH3:14])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]([CH3:14])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

4

Reactant 1

HCID 122026352-(4-Hydroxy-3-nitrophenyl)propanenitrile

Product 1

HCID 122026362-(3-Amino-4-hydroxyphenyl)propanenitrileYield 52.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(3-Nitro-4-hydroxyphenyl) propionitrile (38.4 g., 0.2 mole.) was suspended in absolute ethanol (250 ml.) and hydrogenated at 4 atmospheres pressure and room temperature over 10% palladium on charcoal. Hydrogenation was complete in 3.8 hours. The catalyst was removed by filtration. Evaporation of the filtrate yielded 2-(3-amino-4-hydroxyphenyl) propionitrile (17 g.), m.p. 110° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-b1804e3a9f72420c85d44bd87b4293a2
Source dataset
uspto-grants-1978_04
Patent number
USRE029608

Reaction notes

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