1,4-Dioxane → HCID 19856016, compound

HRID 2073769Notes

Reaction equation

HRID 2073769 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[O:18]1CCOCC1>O>[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH2:9])=[O:18]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 19856008HCID 19856008, compound

Product 1

HCID 19856016HCID 19856016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of 3-amino-2-(4-methoxyphenyl)-4-pyridinecarbonitrile was heated to reflux for 2 hours in 10 ml of water and 10 ml of dioxan in the presence of 4 g of Dowex 1X4-100 (OH form). The resin was removed by filtration and the filtrate was evaporated in order to remove dioxan. The aqueous residue was extracted with ethyl acetate and the organic phase was washed with water and sodium chloride solution, dried over sodium sulphate and evaporated. Recrystallization of the residue from ethyl acetate/hexane yielded 500 mg of 3-amino-2-(4-methoxyphenyl)-4-pyridinecarboxamide as a yellow solid of melting point 179°-181° C.

Workup

  1. customThe resin was removed by filtration
  2. customthe filtrate was evaporated in order
  3. customto remove dioxan
  4. extractionThe aqueous residue was extracted with ethyl acetate
  5. washthe organic phase was washed with water and sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customRecrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8783fa0fa6dc4326a765c3474051f482
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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