6-Fluoro-benzofuran-3-one oxime → 6-Fluoro-2,3-dihydrobenzofuran-3-amine

HRID 1928884Notes

Reaction equation

HRID 1928884 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[N:9]O)[CH2:7][O:8][C:4]=2[CH:3]=1.[H][H]>O1CCCC1.CO.[Ni]>[F:1][C:2]1[CH:12]=[CH:11][C:5]2[CH:6]([NH2:9])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 866341876-Fluoro-benzofuran-3-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 552634306-Fluoro-2,3-dihydrobenzofuran-3-amineYield 33.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above described 6-fluoro-benzofuran-3-one oxime (5.38 g, 32 mmol; HPLC 1.489 min) and Raney-Nickel (2.4 g) in tetrahydrofuran (125 mL) and methanol (125 mL) was hydrogenated at 100 bar hydrogen-pressure at 50° C. for 18 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles very removed in vacuum to give the crude product which was purified by Si—NH2 column chromatography with n-heptane/ethyl acetate to give the title compound as a light brown liquid (1.65 g, 34%, HPLC 0.367 min 100%), MS (ISP) m/e=154.0 [(M+H)+].

Workup

  1. additionA mixture of the
  2. filtrationFiltered the catalyst off,
  3. washwashed with methanol and tetrahydrofuran
  4. customall volatiles very removed in vacuum
  5. customto give the crude product which
  6. customwas purified by Si—NH2 column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-f4a12df88196476ab68f0114dd12cf4e
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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