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

HRID 259555

Reaction equation

HRID 259555 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+]([O-])(OCCC(C)C)=O.[CH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:11]1([C:9]2[O:8][C:6]3[C:5]([N:10]=2)=[CH:4][CH:3]=[C:2]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:7]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 10985Isoamyl nitrateHCID 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 nitrate 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-b544000962be4351a3834cd683a82c26
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Linked notes

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