p-Toluenesulfonic acid → HCID 10154929, compound

HRID 842206Notes

Reaction equation

HRID 842206 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-19041ec62f4244b18e006c9e48446466
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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