Methanol → 6-Amino-5-Fluoro-2-Methylbenzoxazole

HRID 9869

Reaction equation

HRID 9869 reaction equation
[F: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.CO>O1CCCC1>[NH2:12][C:3]1[C:2]([F:1])=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 136277005-Fluoro-2-methyl-6-nitro-1,3-benzoxazole

Product 1

HCID 219887666-Amino-5-Fluoro-2-Methylbenzoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Fluoro-2-methyl-6-nitrobenzoxazole (16 g, 81.57 mMole), was dissolved in tetrahydrofuran (150 mL), and methanol (50 mL). Raney-Nickel which had been pre-washed with water (×3) and tetrahydrofuran (×3), was added and 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 12 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-0a44cb302d4a4d1a9a9ef3a7c37ee2cb
Source dataset
uspto-grants-2006_08
Patent number
US07091361B2

Linked notes

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