Diaminomaleonitrile → HCID 178510651, compound

HRID 2260320Notes

Reaction equation

HRID 2260320 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12](=O)[C:13]([O:15]CCCCCC)=O)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[NH2:23]/[C:24](/[C:29]#[N:30])=[C:25](\[NH2:28])/[C:26]#[N:27]>C(O)C>[OH:15][C:13]1[N:28]=[C:25]([C:26]#[N:27])[C:24]([C:29]#[N:30])=[N:23][C:12]=1[C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 2

HCID 2723951DiaminomaleonitrileHCID 5747978Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, hexyl ester

Product 1

HCID 178510651HCID 178510651, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.0 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 1.5 g of diaminomaleonitrile in 35 ml of ethanol is heated to boiling under reflux for 24 hours. The alcohol is then distilled, the residue is dissolved in ether, washed with water, dried over sodium sulfate, filtered and evaporated. There is obtained 6-hydroxy-5-(3,4-dihydroxy-5-nitrophenyl)-2,3-pyrazinedicarbonitrile of m.p.>300° (from ether/methylene chloride).

Workup

  1. temperatureunder reflux for 24 hours
  2. distillationThe alcohol is then distilled
  3. dissolutionthe residue is dissolved in ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-571a26c7f1d9475280ab4718905b6575
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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