HCID 3089143, compound → 2-(4-Amino-phenyl)-benzooxazol-5-ylamine

HRID 1599014Notes

Reaction equation

HRID 1599014 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(OC(O)C)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:13]=3[N:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3089143HCID 3089143, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 6143852-(4-Amino-phenyl)-benzooxazol-5-ylamineYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 101298981-EthoxyethanolSolvent

Procedure

2-(4-Nitrophenyl)-5-nitrobenzoxazole (30 g, 0.105 mol), ethoxyethanol (300 mL) and 10 percent Pd/C (300 mg) were placed in a 600 mL Parr Reactor. The reactor was heated to 70° C. at 50 psi hydrogen (340 kPa) for 3 hours, then 90° C. at 150 psi hydrogen (1033 kPa) for an additional 16 hours. After the hydrogen was vented off, the solution was filtered hot under nitrogen. A portion of the solvent (100 mL) was removed from the solution and deionized water (100 mL) was added thereto, causing product to precipitate. The solution containing the precipitated product was stirred and refluxed for 1 hour. The solution was cooled to room temperature, and the product was filtered and washed with methanol (50 mL). The product was dried and 20.7 g (87 percent yield) of an off-white solid having a melting point of 226° C. to 228° C. was obtained.

Workup

  1. filtrationthe solution was filtered hot under nitrogen
  2. customA portion of the solvent (100 mL) was removed from the solution
  3. additionwas added
  4. customto precipitate
  5. additionThe solution containing the precipitated product
  6. temperaturerefluxed for 1 hour
  7. filtrationthe product was filtered
  8. washwashed with methanol (50 mL)
  9. customThe product was dried

Sources & evidence

ORD record
ord-f1c2b38556474baab2cbed6847efd97f
Source dataset
uspto-grants-1998_04
Patent number
US05739344

Reaction notes

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