HCID 21310722, compound → HCID 21310721, compound

HRID 583185Notes

Reaction equation

HRID 583185 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([N+:12]([O-])=O)[CH:3]=1>[Fe].CC(O)=O>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([NH2:12])[CH:3]=1

Participants

4

Reactant 1

HCID 21310722HCID 21310722, compound

Product 1

HCID 21310721HCID 21310721, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 720 mg of 4-bromo-2-methyl-6-nitro-benzooxazole in 45 mL ETOH was added 642 mg of iron powder and 8.5 mL of AcOH. Solution was refluxed for 2.5 h, during which a chalky white color formed. Solvent was removed, solid was dissolved back into DCM and filtered through Celite. The filtrate was washed with satd. NaHCO3 and brine, dried over MgSO4, and solvent evaporated. 690 mg of title compound as a brown solid was recovered.

Workup

  1. temperatureSolution was refluxed for 2.5 h, during which a chalky white color
  2. customformed
  3. customSolvent was removed
  4. dissolutionsolid was dissolved back into DCM
  5. filtrationfiltered through Celite
  6. washThe filtrate was washed with satd
  7. dry with materialNaHCO3 and brine, dried over MgSO4, and solvent
  8. customevaporated
  9. custom690 mg of title compound as a brown solid was recovered

Sources & evidence

ORD record
ord-04d47781664e4d98861a2b8013f18790
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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