Ammonium Chloride → 4-(1,2,4-Oxadiazol-3-yl)aniline

HRID 1665619Notes

Reaction equation

HRID 1665619 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][O:14][N:13]=2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Zn]>[O:14]1[CH:15]=[N:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=2)=[N:13]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 27982883-(4-Nitrophenyl)-1,2,4-oxadiazole

Product 1

HCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineYield 96.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (214 mg, 4 mmol) in water (5 mL) was added to a stirred solution of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole (200 mg, 1 mmol) in THF (15 mL). Zinc powder (262 mg, 4 mmol) was then added portion wise. The reaction was stirred at room temperature for 1 hour and then refluxed at 65° C. for 5 hours. The mixture was filtered over celite, the filtrate was evaporated and the residue was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated to afford 155 mg (92%) of 4-[1,2,4]oxadiazol-3-yl-phenylamine. 1H NMR: (DMSO-d6): δ 9.5 (s, 1H), 7.7 (d, 2H), 6.7 (d, 2H), 5.8 (s, 2H).

Workup

  1. temperaturerefluxed at 65° C. for 5 hours
  2. filtrationThe mixture was filtered over celite
  3. customthe filtrate was evaporated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe ethyl acetate was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-fd8a93ad09ba4013be5ac8549662c757
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

Loading…