Ammonia → 5-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-1,3,4-oxadiazol-2(3H)-one

HRID 1164811Notes

Reaction equation

HRID 1164811 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](=[O:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.O1[CH:19]=[CH:18][C:17](=[O:20])[CH:16]=[CH:15]1.Cl.N>O>[O:20]=[C:17]1[CH:18]=[CH:19][N:1]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[O:12][C:11](=[O:13])[NH:10][N:9]=3)=[CH:6][CH:7]=2)[CH:15]=[CH:16]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 79684H-pyran-4-oneHCID 2796305-(4-aminophenyl)-1,3,4-oxadiazol-2-ol

Product 1

HCID 197942235-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-(4-aminophenyl)-1,3,4-oxadiazol-2(3H)-one (0.41 g), 4H-pyran-4-one (0.24 g), and hydrochloric acid (2N, 1.15 ml) in water (25 ml) was stirred under reflux for 3 hours to afford a yellow solid. This solid was added to hot water with stirring and the resulting suspension was made alkaline (pH 8) with aqueous ammonia and was then filtered. The collected solid was dissolved in aqueous potassium carbonate and the resulting solution was neutralised with dilute acetic acid to afford an emulsion from which after centrifugation was obtained the title compound, 0.47 g, m.p. 220° C. (decomp), contaminated with potassium acetate.

Workup

  1. temperatureunder reflux for 3 hours
  2. customto afford a yellow solid
  3. stirringwith stirring
  4. filtrationwas then filtered
  5. dissolutionThe collected solid was dissolved in aqueous potassium carbonate
  6. customto afford an emulsion from which after centrifugation

Sources & evidence

ORD record
ord-deeae95e43094f4fadd4e8c0dbd2d4bb
Source dataset
uspto-grants-1990_03
Patent number
US04906628

Reaction notes

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