2,5-Pyridinedicarboxylic acid → N,N,N',N'-tetraisoamyl pyridine-2,5-dicarboxamide

HRID 1650123Notes

Reaction equation

HRID 1650123 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[CH:3][C:2]=1[C:10]([OH:12])=O.[CH2:13]([NH:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:14][CH:15]([CH3:17])[CH3:16]>>[CH2:19]([N:18]([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:10]([C:2]1[CH:3]=[CH:4][C:5]([C:7]([N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])=[O:9])=[CH:6][N:1]=1)=[O:12])[CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 74932,5-Pyridinedicarboxylic acidHCID 10988Diisoamylamine

Product 1

HCID 23053580N,N,N',N'-tetraisoamyl pyridine-2,5-dicarboxamide

Procedure

N,N,N',N'-tetraisoamyl pyridine-2,5-dicarboxamide was prepared using the method of Example 1 from pyridine-2,5-dicarboxylic acid and diisoamylamine. The crude product in toluene solution was washed several times with 0.5M aqueous sodium hydroxide and then with 0.5M aqueous hydrochloric acid and water. The solution was then treated with charcoal and filtered. The solvent was distilled under reduced pressure, but the product, a brown oil, was not itself distilled. It was made up as a 0.2M solution in AROMASOL H and tested for extraction of copper in the presence of chloride ion using the method of Examples 6 and 7 except that AROMASOL H was used as solvent. The results are given in Table 3. The results indicate that this is a very weak extractant suitable for recovering copper from aqueous solution of high chloride ion concentrations.

Workup

  1. washThe crude product in toluene solution was washed several times with 0.5M aqueous sodium hydroxide
  2. additionThe solution was then treated with charcoal
  3. filtrationfiltered
  4. distillationThe solvent was distilled under reduced pressure
  5. distillationdistilled
  6. extractiontested for extraction of copper in the presence of chloride ion using the method of Examples 6 and 7 except that AROMASOL H
  7. customfor recovering copper
  8. concentrationfrom aqueous solution of high chloride ion concentrations

Sources & evidence

ORD record
ord-0bb310a0fc3445caa35d26eff596d4da
Source dataset
uspto-grants-1990_05
Patent number
US04923686

Reaction notes

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