HCID 23442070, compound → HCID 10711354, compound

HRID 1417348Notes

Reaction equation

HRID 1417348 reaction equation
[N+:1]([C:4]1[C:5]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])=[N:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:5]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])=[N:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 23442070HCID 23442070, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10711354HCID 10711354, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To 3,3'-[3-nitro-2,6-pyridinediylbis(oxy)]bis(benzonitrile) (18.5 g, 50 mmol) dissolved in ethanol/ethyl acetate (500 mL, 2/3) was added 10% palladium on carbon (1.8 g). After subjecting the mixture to hydrogen at 15 psi for 2 hours, the reaction was suction filtered through celite. The solvent was removed in vacuo to give 3,3'-[3-amino-2,6-pyridinediylbis(oxy)]bis(benzonitrile); NMR (CDCl3) 7.5 (m,7), 7.2 (m,2), 6.6 (d,1), 3.8 (br,2) ppm.

Workup

  1. customfor 2 hours
  2. filtrationfiltered through celite
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-af0732ab164c4c90954380f12a80c83e
Source dataset
uspto-grants-1999_03
Patent number
US05877181

Reaction notes

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