p-Toluenesulfonic acid → HCID 10154929, compound

HRID 413918Notes

Reaction equation

HRID 413918 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=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:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[C:16]=1[CH3:17])=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 778882-Amino-5-nitropyridineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 10154929HCID 10154929, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Nitro-pyridin-2-ylamine (5 mmol, 0.7 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 solid was triturated with chloroform, the filtrate was further purified over silica gel to yield the named product, 1H-NMR (CDCl3, ppm) 1.35 t (3H), 2.54 s (3H), 4.30 q (2H), 6.78 s (1H), 6.96-7.25 bm (6H), 8.33 dd (1H), 9.39 sd (1H)

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe resulting solid was triturated with chloroform
  4. customthe filtrate was further purified over silica gel
  5. customto yield the named product, 1H-NMR (CDCl3, ppm) 1.35 t (3H), 2.54 s (3H), 4.30 q (2H), 6.78 s (1H), 6.96-7.25 bm (6H), 8.33 dd (1H), 9.39

Sources & evidence

ORD record
ord-5264e31f71d448f6802837fb7bb25c70
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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