Hydrochloric Acid → 4-[3-(2-Furanyl)-1,2,4-oxadiazol-5-yl]benzenamine

HRID 462175Notes

Reaction equation

HRID 462175 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[O:8][N:7]=1.Cl.C([O-])([O-])=O.[K+].[K+]>[Pd]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[O:8][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21390710HCID 21390710, compound

Product 1

HCID 230082014-[3-(2-Furanyl)-1,2,4-oxadiazol-5-yl]benzenamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 3-(2-furyl)-5-(4-nitrophenyl)-1,2,4-oxadiazole (8.0 g, 0.03 mole) in 200 ml of absolute alcohol containing 5.2 ml of concentrated HCl is hydrogenated using 0.5 g of 5% Pd on carbon as catalyst. The solid obtained is slurried with saturated K2CO3 solution and extracted with CHCl3. Evaporation of the CHCl3 in vacuo gives the amine, 5.1 g (72%), m.p. 183°-185°.

Workup

  1. customThe solid obtained
  2. extractionextracted with CHCl3
  3. customEvaporation of the CHCl3 in vacuo

Sources & evidence

ORD record
ord-af480058bb0a46bb80633a4151abf274
Source dataset
uspto-grants-1977_12
Patent number
US04065563

Reaction notes

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