Water → 2-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

HRID 2212334Notes

Reaction equation

HRID 2212334 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[C:15]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:13][N:12]=1.O>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[C:1]([NH:10][C:11]1[CH:16]=[C:15]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:13][N:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 219641952-(2-Amino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanoneYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

Benzoyl chloride (4.4 g, 31 mmol) and 4-dimethylaminopyridine (0.57 g, 4.7 mmol) were added to a solution of 2-(2-amino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (3.8 g, 16 mmol) in N,N-dimethylacetamide (80 mL) and the mixture was stirred at 70° C. for 12 hours. After the reaction mixture was cooled to room temperature, water (50 mL) was added. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The layer was dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in tetrahydrofuran (80 mL) and methanol (20 mL) and 1N-aqueous solution of sodium hydroxide (50 mL) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and water (100 mL) was added. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The layer was dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain 3.1 g of the title compound (8.9 mmol, yield 57%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialThe layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (80 mL)
  8. additionmethanol (20 mL) and 1N-aqueous solution of sodium hydroxide (50 mL) was added
  9. stirringThe mixture was stirred at room temperature for 3 hours
  10. concentrationThe reaction mixture was concentrated
  11. additionwater (100 mL) was added
  12. extractionThe mixture was extracted with ethyl acetate
  13. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialThe layer was dried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b1f8d320966c4ec4a3fcb45dadca1237
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

Loading…