p-Toluenesulfonic acid → HCID 9903064, compound

HRID 842196Notes

Reaction equation

HRID 842196 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]([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:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=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 778882-Amino-5-nitropyridineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 9903064HCID 9903064, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Nitro-2-aminopyridine (5 mmol, 0.7 g), 2-benzoyl-4-oxo-pentanoic 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, and the insoluble material filtered from the reaction mixture. The filtrate was purified over silica gel and yielded the named product (m.p. 146.6° C.-148.6° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe resulting solid was triturated with chloroform
  4. filtrationthe insoluble material filtered from the reaction mixture
  5. customThe filtrate was purified over silica gel

Sources & evidence

ORD record
ord-bd88991deeab40788b9cc45daa00290a
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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