p-Toluenesulfonic acid → HCID 2742307, compound

HRID 413916Notes

Reaction equation

HRID 413916 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]([CH2:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16](=O)[CH3:17])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:19]=[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]([C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:16]=1[CH3:17])=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74754-NitroanilineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 2742307HCID 2742307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

p-Nitroaniline (5 mmol, 0.7 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.25 g), and tosic acid were combined in ethanol, then heated under reflux. The reaction mixture was cooled on ice (0-5° C.), and the precipitate filtered from the reaction mixture. 1H-NMR analysis confirmed that the precipitate was the named product, (CDCl3, ppm); 1.38 t (3H), 2.45 s (3H), 4.20 q (2H), 6.80 s (1H), 6.97-7.35 bm (7H), 8.25 d (2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationthe precipitate filtered from the reaction mixture
  4. custom1.38 t (3H), 2.45 s (3H), 4.20 q (2H), 6.80 s (1H), 6.97-7.35 bm (7H), 8.25 d (2H)

Sources & evidence

ORD record
ord-9aa1246b83694aa4890b6686cb720c34
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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