p-Toluenesulfonic acid → HCID 9857704, compound

HRID 413903Notes

Reaction equation

HRID 413903 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-da8119b58432454e9ae3ae5b6fd82cdb
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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