Benzene → 2,5-Diphenyloxazolo[5,4-b]pyridine

HRID 66367Notes

Reaction equation

HRID 66367 reaction equation
N[C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.N(OCCC(C)C)=O.[CH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:11]1([C:9]2[O:8][C:6]3[C:5]([N:10]=2)=[CH:4][CH:3]=[C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:7]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 8053Isoamyl NitriteHCID 227547935-Amino-2-phenyloxazolo[5,4-b]pyridine

Product 1

HCID 156656752,5-Diphenyloxazolo[5,4-b]pyridine

Procedure

A mixture of 180 mg. of 5-amino-2-phenyloxazolo[5,4-b]pyridine, 10 ml. of benzene and 0.2 ml. of isoamyl nitrite was refluxed for 11/2 hours. The hot solution was filtered and concentrated to dryness. The residue was extracted with ether and the extract was filtered through aluminum oxide and concentrated to dryness. The crystalline residue was recrystallized from ethyl acetate to give 2,5-diphenyloxazolo[5,4-b]pyridine, m.p. 151°-152° C.

Workup

  1. additionA mixture of 180 mg
  2. filtrationThe hot solution was filtered
  3. concentrationconcentrated to dryness
  4. extractionThe residue was extracted with ether
  5. filtrationthe extract was filtered through aluminum oxide
  6. concentrationconcentrated to dryness
  7. customThe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cf1c4c6860414ee0856bff9eb2556529
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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