p-Toluenesulfonic acid → HCID 10132536, compound

HRID 842197Notes

Reaction equation

HRID 842197 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:11]([O:13][C:14](=[O:28])[CH:15]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17](=O)[CH3:18])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH3:18])[N:1]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74193-Aminobenzoic AcidHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 10132536HCID 10132536, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminobenzoic acid (10 mmol, 1.4 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (10 mmol, 2.5 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in chloroform-ether, then the insoluble material was filtered from the reaction product. The soluble material was purified over silica gel which yielded the named product (m.p. 161.0° C.-162.7° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationthe insoluble material was filtered from the reaction product
  4. customThe soluble material was purified over silica gel which

Sources & evidence

ORD record
ord-242a180e822b4dac931d88d36e4cf664
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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