Ammonium Chloride → 4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline

HRID 1665623Notes

Reaction equation

HRID 1665623 reaction equation
[Cl-].[NH4+].[CH3:3][C:4]1[O:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[N:7][N:8]=1>O.C1COCC1.[Zn]>[CH3:3][C:4]1[O:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:7][N:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 5404162-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

Product 1

HCID 195422444-(5-Methyl-1,3,4-oxadiazol-2-yl)anilineYield 48.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (1.12 g, 21 mmol) in water (5 mL) was added to a stirred solution of 2-methyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole (530 mg, 2.6 mmol) in THF (10 mL). Zinc powder (1.4 g, 21 mmol) was added portion wise and the mixture was stirred at room temperature for 1 hour then heated to reflux at 65° C. for 5 hours. The mixture was then filtered over celite and the filtrate was concentrated. The residue was extracted with ethyl acetate and the organics were washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (4% methanol in chloroform) to afford 220 mg (48%) of 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl amine. 1H NMR: (CDCl3): δ 7.8 (d, 2H), 6.7 (d, 2H), 4.0 (s, 2H), 2.6 (s, 3H).

Workup

  1. temperaturethen heated
  2. temperatureto reflux at 65° C. for 5 hours
  3. filtrationThe mixture was then filtered over celite
  4. concentrationthe filtrate was concentrated
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe organics were washed with brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2be3ad5d39744470b8304ae12a135c91
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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