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

HRID 411954

Reaction equation

HRID 411954 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-498e10bbd86a4e8c90610cd9b296b4ea
Source dataset
uspto-grants-2003_05
Patent number
US06562558B1

Linked notes

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