3-Benzoylamino-5-nitro-2-pyridone → 6-Nitro-2-phenyloxazolo[5,4-b]pyridine

HRID 1886908Notes

Reaction equation

HRID 1886908 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=O)[NH:8][CH:9]=1)([O-:3])=[O:2]>O>[N+:1]([C:4]1[CH:5]=[C:6]2[N:11]=[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:19][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 227547673-Benzoylamino-5-nitro-2-pyridone

Product 1

HCID 251880586-Nitro-2-phenyloxazolo[5,4-b]pyridineYield 3.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

To polyphosphoric acid at 165° C. was added N-(5-nitro-2-oxo-1,2-dihydropyridin-3-yl)benzamide (300 mg, 1.16 mmol). The resulting mixture was then heated to 165° C. for 30 min. The solution was then poured into water. The resulting precipitate was collected by filtration, dissolved in diethyl ether, filtered through alumina and evaporated to afford 9 mg (3%) of the title compound.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in diethyl ether
  3. filtrationfiltered through alumina
  4. customevaporated

Sources & evidence

ORD record
ord-464964aa59454d56b416f9a720bfa095
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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