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

HRID 9865Notes

Reaction equation

HRID 9865 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

5-Chloro-2-methyl-6-nitrobenzoxazole (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 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-dfe50d41f12942da8b2bfc15e4f89f80
Source dataset
uspto-grants-2006_08
Patent number
US07091361B2

Reaction notes

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