p-Toluenesulfonic acid → HCID 9901134, compound

HRID 413915Notes

Reaction equation

HRID 413915 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]([C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][C:14](=O)[CH3:15])[CH3:9].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:8]([O:10][C:11]([C:12]1[CH:13]=[C:14]([CH3:15])[N:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:17]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:25])[CH3:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 100093-AminopyridineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 9901134HCID 9901134, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminopyridine (5 mmol, 0.5 g), 2-benzoyl-4-oxo-pentanoic 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 purified over silica, but still contained contaminants. This material was triturated in hexane, and the solids were separated by filtration. The solids were washed with benzene two times to yield the named product (m.p. 102° C.-103° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe resulting oil was purified over silica, but still contained contaminants
  4. customThis material was triturated in hexane
  5. customthe solids were separated by filtration
  6. washThe solids were washed with benzene two times

Sources & evidence

ORD record
ord-cc3e0d10bc464c54b86a885a10859350
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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