HCID 22724333, compound → HCID 22724291, compound

HRID 2086779Notes

Reaction equation

HRID 2086779 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CO.O1CCOCC1>[NH2:1][C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 22724333HCID 22724333, compound

Product 1

HCID 22724291HCID 22724291, compoundYield 88.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-nitro-2-((E)-3-styrylphenylamino)pyridine (1.03 g) and 10% palladium on carbon (0.3 g) in methanol (20 ml) and 1,4-dioxane (20 ml) was stirred under hydrogen (3 atm) at room temperature for 1.5 hours. The catalyst was removed by filtration and the solvent was evaporated. The resulting solid was collected and washed with isopropyl ether to give 3-amino-2-(3-phenethylphenylamino)pyridine (835 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe resulting solid was collected
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-2e23bb33dd174b2a9ef7ca59cbd421d9
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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