5-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one → 5-(2-Aminophenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 378968

Reaction equation

HRID 378968 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13](=[O:15])[NH:12][N:11]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13](=[O:15])[NH:12][N:11]=1

Participants

4

Reactant 1

HCID 3129215-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one

Product 1

HCID 128581485-(2-Aminophenyl)-1,3,4-oxadiazol-2(3H)-oneYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitrobenzoylhydrazine (9.05 g, 0.05 mol) in dioxane (30 mL) was slowly added to a solution of trichloromethyl chloroformate (4.6 mL, 0.04 mol) in dioxane (30 mL) at room temperature. On completion of the addition the reaction was heated to reflux for 4 hours. The solvent was evaporated off and the residue re-crystallised from 96%. ethanol (50 mL) to give 7.15 g of the 5-(2-nitrophenyl)-3H-[1,3,4]oxadiazol -2-one. M.p. 157-158° C. A solution of the nitro compound (2 g, 9.7 mmol) in 96% ethanol (25 mL) was hydrogenated over 5% palladium on charcoal to give desired 1.6 g of the desired amine.

Sources & evidence

ORD record
ord-f78aa3592ecc4746adebbabc51b8c5ee
Source dataset
uspto-grants-2001_10
Patent number
US06297261B1

Linked notes

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