Ethylenediamine → HCID 15066358, compound

HRID 477770Notes

Reaction equation

HRID 477770 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C(N)[CH2:17][NH2:18]>CN(C)C=O.O>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:17]#[N:18])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 19861001HCID 19861001, compound

Product 1

HCID 15066358HCID 15066358, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,6 g (5,9 mmol) 1-amino-5-bromo-2-nitronaphthalene in 50 ml dimethylformamide was added 1,1 g (11,8 mmol) cuprous cyanide. The reaction mixture was refluxed for 5 h, and then poured into a solution of 2,5 ml ethylenediamine in 80 ml water. Stirring was continued for 15 min., and then the precipitate was filtered off and washed with water and boiling ethyl acetate to give 1,0 g (80%) 1-amino-5-cyano-2-nitronaphthalene.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-f680de755e4e4c94b4bbce2e2b47605a
Source dataset
uspto-grants-1989_12
Patent number
US04889855

Reaction notes

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