Isoniazid → 4-(1,3,4-Oxadiazol-2-yl)pyridine

HRID 1765675Notes

Reaction equation

HRID 1765675 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC(OCC)OCC)C>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[O:8][CH:11]=[N:10][N:9]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 6101p-Toluenesulfonic acid

Product 1

HCID 7756364-(1,3,4-Oxadiazol-2-yl)pyridineYield 57,738.301%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the isonicotinic hydrazide (13.7 g, 100 mmol), triethylorthoformate (60 ml) and p-toluenesulfonic acid (30 mg) was heated at 130° C. for 12 hours. Excess triethylorthoformate was removed under vacuum. The residue was crystallized from ethyl acetate to give 2-(4-pyridyl)-[1,3,4]oxadiazole (14.8 g); H1 NMR [(CD3)2SO]: δ 9.46 (1H, s), 8.8 (2H, dd), 7.9 (2H, dd).

Workup

  1. customExcess triethylorthoformate was removed under vacuum
  2. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-618527cd194e4317aa66250c1a1c16d1
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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