1-Naphthalenamine, 5-nitro- → 1,5-Diaminonaphthalene

HRID 49657

Reaction equation

HRID 49657 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[NH2:14])([O-])=O.[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:4]1([NH2:1])[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:14])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 767591-Naphthalenamine, 5-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 167201,5-DiaminonaphthaleneYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

8.20 g of 5-nitro-1-naphthylamine (43.6 mmol) in 35 ml of toluene are placed in a 0.1 liter autoclave with 0.5 g of palladium on carbon (5%) and hydrogenated at 50° C. and 40 bar hydrogen pressure for 5 h, stirring. On completion of the reaction, the cooled autoclave is depressurised and the catalyst is filtered off. With a quantitative conversion, 6.72 g of 1,5-naphthalenediamine (42.5 mmol, 97.5%) are formed.

Workup

  1. customOn completion of the reaction
  2. filtrationthe catalyst is filtered off

Sources & evidence

ORD record
ord-792bac47a14e49bca7915abc5c568f62
Source dataset
uspto-grants-2004_03
Patent number
US06706924B2

Linked notes

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