1-Nitronaphthalene → 4-Nitro-1-naphthylamine

HRID 257598

Reaction equation

HRID 257598 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].[Cl-].[NH4+:17]>CS(C)=O>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([NH2:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 68491-NitronaphthaleneHCID 14797Potassium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 130574-Nitro-1-naphthylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

3.5 g of 1-nitronaphthalene and 3.3 g of N,N-tetramethylenethiocarbamoylsulphenamide, dissolved in 15 ml of dimethyl sulphoxide, are added dropwise to a vigorously stirred suspension of 6 g of potassium hydroxide in 50 ml of dimethyl sulphoxide, the temperature being kept at 20° to 25° C. When the addition has ended the mixture is stirred for a further 60 minutes, poured into 400 ml of a saturated aqueous ammonium chloride solution and extracted with methylene chloride. After drying and removing the solvent, 4-nitro-1-naphthylamine is obtained with a melting point of 190° to 192° C. The yield is 2.9 g (77%). 1Nitro-2-napthylamine is additionally obtained in a yield of about 2%.

Workup

  1. custombeing kept at 20° to 25° C
  2. additionWhen the addition
  3. extractionextracted with methylene chloride
  4. customAfter drying
  5. customremoving the solvent

Sources & evidence

ORD record
ord-7974db6dad9b4a9cad76e2dd880c957c
Source dataset
uspto-grants-1993_11
Patent number
US05262539

Linked notes

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