p-Toluenesulfonic acid → HCID 9946388, compound

HRID 413917Notes

Reaction equation

HRID 413917 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([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:6]([C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])[C:16]=1[CH3:17])=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69462-NitroanilineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 9946388HCID 9946388, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Nitroaniline (15 mmol, 2.1 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (15 mmol, 3.7 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was purified over three silica gel columns to yield the named product, 1H-NMR (CDCl3, ppm): 1.36 t (3H), 2.36 s (3H), 4.31 q (2H), 6.80 s (1H), 7.03-7.66 bm (6H), 7.68 dt (2H), 7.97 dd (1H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe resulting oil was purified over three silica gel columns
  4. customto yield the named product, 1H-NMR (CDCl3, ppm): 1.36 t (3H), 2.36 s (3H), 4.31 q (2H), 6.80 s (1H), 7.03-7.66 bm (6H), 7.68 dt (2H), 7.97 dd (1H)

Sources & evidence

ORD record
ord-84ed3639cd3e4c90b7d40b43ea2a21ec
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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