1-Nitronaphthalene → 2-Naphthylamine, 1-nitro-

HRID 257599

Reaction equation

HRID 257599 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].[Cl-].[NH4+:15]>CN(C)C=O>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH2:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 68491-NitronaphthaleneHCID 25517Ammonium Chloride

Product 1

HCID 118232-Naphthylamine, 1-nitro-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.5 g of 1-nitronaphthalene and 3.7 g of benzthiazyl-2-sulphenamide, dissolved in 30 ml of dimethylformamide, are added dropwise to a stirred solution of 6 g of potassium tert.-butylate in 60 ml of dimethylformamide, while the temperature is kept at 20° to 25° C. After stirring further for 15 minutes the mixture is poured into 400 ml of a saturated aqueous ammonium chloride solution and then treated further as in Example 1. 1-Nitro-2-naphthylamine with a melting point of 123° to 125° C. is obtained in a yield of 2.9 g (72%). In addition, about 8% of 4-nitro-1-naphthylamine are obtained.

Workup

  1. customis kept at 20° to 25° C
  2. additiontreated further as in Example 1

Sources & evidence

ORD record
ord-9e17187bb68d42d1a3042acc2a8533e8
Source dataset
uspto-grants-1993_11
Patent number
US05262539

Linked notes

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