Ammonium Chloride → 2-(4-Methylphenyl)-1,3-benzoxazol-6-amine

HRID 1896745Notes

Reaction equation

HRID 1896745 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:14]1([CH3:17])[CH:13]=[CH:12][C:11]([C:9]2[O:10][C:6]3[CH:5]=[C:4]([NH2:1])[CH:19]=[CH:18][C:7]=3[N:8]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 12251550HCID 12251550, compound

Product 1

HCID 164792462-(4-Methylphenyl)-1,3-benzoxazol-6-amineYield 4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To 6-nitro-2-p-tolylbenzo[d]oxazole (2.1 g, 8.27 mmol) in ethanol:water 2:1 v/v (60 mL) at 70° C. was added iron powder (2.14 g, 38.3 mmol) and ammonium chloride (819 mg, 15.3 mmol). The suspension was stirred at reflux for 16 h. After cooling, the solution was filtered through a pad of Celite® and washed with ethanol. After evaporation of the solvent, the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate:hexanes 1:3 v/v to afford 70 mg (4%) of the title compound (LCMS RT=6.12 min, MH+ 223.1)

Workup

  1. temperatureat reflux for 16 h
  2. temperatureAfter cooling
  3. filtrationthe solution was filtered through a pad of Celite®
  4. washwashed with ethanol
  5. customAfter evaporation of the solvent
  6. extractionthe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. customevaporated
  9. customThe resulting solid was purified by column chromatography
  10. washeluting with ethyl acetate:hexanes 1:3 v/v

Sources & evidence

ORD record
ord-b49bff113ea6474193efa7fd202d0c5e
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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