Ethylenediamine → HCID 15066358, compound

HRID 1165820Notes

Reaction equation

HRID 1165820 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, m.p. 260-262° C. IR (KBr): 2200 cm-1 (nitrile function).

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-dcaf439227a84d25a2cf385340d7b272
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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