p-Toluenesulfonic acid → HCID 9857704, compound

HRID 842192Notes

Reaction equation

HRID 842192 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([O:10][C:11](=[O:25])[CH:12]([CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13](=O)[CH3:14])[CH3:9].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.CCOCC>[CH2:8]([O:10][C:11]([C:12]1[CH:16]=[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:13]=1[CH3:14])=[O:25])[CH3:9]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 100093-AminopyridineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 9857704HCID 9857704, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Aminopyridine (5 mmol, 0.5 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g) and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in ether, then washed with water and brine. The organic layer was dried over MgSO4, then the solids were separated and the solvents were removed under vacuum. The named product was purified over silica gel and analyzed by 1H-NMR (CDCl3, ppm): 1.35 t (3H), 2.40 s (3H), 4.3 q (2H), 6.78 s (1H), 7.03-7.39 m (7H), 8.4 sd (1H), and about 8.6 dd (1H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solids were separated
  6. customthe solvents were removed under vacuum
  7. customThe named product was purified over silica gel

Sources & evidence

ORD record
ord-81acf4a7129c4440adbf39546f768818
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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