p-Toluenesulfonic acid → HCID 9924533, compound

HRID 413919Notes

Reaction equation

HRID 413919 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[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:8]([C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=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 74754-NitroanilineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 9924533HCID 9924533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Nitroaniline (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 reaction mixture was filtered and the solids washed with ethanol. The collected material was determined to be the named product (m.p. 190° C.-192° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was filtered
  4. washthe solids washed with ethanol

Sources & evidence

ORD record
ord-272c1f583e194a78bea0cde80903bf9b
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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