1,4-Dioxane → HCID 21957378, compound

HRID 2073767Notes

Reaction equation

HRID 2073767 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[O:16]1CCOCC1>O>[NH2:1][C:2]1[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH2:9])=[O:16]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 198560113-Amino-2-phenylpyridine-4-carbonitrile

Product 1

HCID 21957378HCID 21957378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of 3-amino-2-phenyl-4-pyridinecarbonitrile was heated to reflux for 3.5 hours in 20 ml of water and 10 ml of dioxan in the presence of 4 g of Amberlite lRA-400-OH (basic form). The resin was removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate (1:19) for the elution and the product was recrystallized from ethyl acetate/petroleum ether to yield 900 mg of 3-amino-2-phenyl-4-pyridinecarboxamide of melting point 163°-164° C.

Workup

  1. customThe resin was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution
  5. customthe product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-92fd5e34e8b54d0ca67f965948020715
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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