p-Toluenesulfonic acid → HCID 9901134, compound

HRID 842203Notes

Reaction equation

HRID 842203 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-da1b880bab114ea29555a688bab36e46
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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