5-Chloro-2-methyl-6-nitro-1,3-benzoxazole → 2-Methyl-5-chloro-6-benzoxazolamine

HRID 1935301Notes

Reaction equation

HRID 1935301 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-])=O)=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1>O1CCCC1>[NH2:12][C:3]1[C:2]([Cl:1])=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

3

Reactant 1

HCID 27644555-Chloro-2-methyl-6-nitro-1,3-benzoxazole

Product 1

HCID 112754042-Methyl-5-chloro-6-benzoxazolamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound (2), (30 g), was dissolved in tetrahydrofuran (150 mL), and Raney-Nickel which had been pre-washed with water (×3) and tetrahydrofuran (×3), was added. The mixture was then hydrogenated at room temperature and 352 kg/dm2 (50 psi) of hydrogen. The reaction is complete in approximately 1.5 hours. After this period, the catalyst is filtered off and the solution concentrated under reduced pressure. The residue is triturated with heptane, cooled and the solid filtered off. Yield 22 g.

Workup

  1. washRaney-Nickel which had been pre-washed with water (×3) and tetrahydrofuran (×3)
  2. additionwas added
  3. customwas then hydrogenated at room temperature
  4. waitAfter this period
  5. filtrationthe catalyst is filtered off
  6. concentrationthe solution concentrated under reduced pressure
  7. customThe residue is triturated with heptane
  8. temperaturecooled
  9. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-91d1ce91fc304c9da92856bfff2ca1c7
Source dataset
uspto-grants-2002_05
Patent number
US06387606B1

Reaction notes

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