5-(2-Methoxy-4-nitrophenyl)oxazole → 3-Methoxy-4-(oxazol-5-yl)aniline

HRID 1984968Notes

Reaction equation

HRID 1984968 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[O:16][CH:15]=[N:14][CH:13]=1.[H][H]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[O:16][CH:15]=[N:14][CH:13]=1

Participants

4

Reactant 2

HCID 101983405-(2-Methoxy-4-nitrophenyl)oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Compound 2f (50 g, 1.0 eq., Nippon Soda) and 1% Pt, 2% V on C (2.78 g, 64% wet, 2.0 wt % on a dry basis, Degussa Type CF1082) were charged to a hydrogenation vessel under nitrogen. Ethyl acetate (500 ml, 10 vol) was added and the mixture was heated to 60° C. The vessel was pressurized with hydrogen (1.00 bar overpressure) and the mixture was stirred at 60° C. The reaction was complete within 3 hours. The pressure was released and nitrogen was bubbled through the reaction mixture. The reaction mixture was filtered through Celite® and washed with EtOAc (100 ml, 2 vol). The solvent level was reduced to 4 vol by distillation at reduced pressure and toluene (500 ml, 10 vol) was charged into the vessel. The solvent level was reduced to 4 vol by distillation at reduced pressure and a second portion of toluene (500 ml, 10 vol) was charged into the vessel. The solvent level was reduced to 5 vol under reduced pressure then the mixture was heated to 90° C. at atmospheric pressure to dissolve any solids. The solution was then cooled slowly to 20° C. to induce crystallization. The resulting yellow solid was filtered and washed with toluene (100 ml, 2 vol) to give compound 2g which was dried in a vacuum oven at 50° C. with a nitrogen bleed until a constant weight of 39.4 g (91%) was achieved.

Workup

  1. customnitrogen was bubbled through the reaction mixture
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with EtOAc (100 ml, 2 vol)
  4. distillationThe solvent level was reduced to 4 vol by distillation at reduced pressure and toluene (500 ml, 10 vol)
  5. additionwas charged into the vessel
  6. distillationThe solvent level was reduced to 4 vol by distillation at reduced pressure
  7. additiona second portion of toluene (500 ml, 10 vol) was charged into the vessel
  8. temperaturethe mixture was heated to 90° C. at atmospheric pressure
  9. dissolutionto dissolve any solids
  10. temperatureThe solution was then cooled slowly to 20° C.
  11. customcrystallization
  12. filtrationThe resulting yellow solid was filtered
  13. washwashed with toluene (100 ml, 2 vol)

Sources & evidence

ORD record
ord-f194ea53123e47e98f9863f75250a8ca
Source dataset
uspto-grants-2009_06
Patent number
US07544810B2

Reaction notes

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