Ammonium formate → 8-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 548765Notes

Reaction equation

HRID 548765 reaction equation
Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:15].C([O-])=O.[NH4+]>[Pd].CO>[F:15][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:14])[N:8]([CH3:13])[CH2:9][CH2:10][O:11][C:12]=2[CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 576632269-chloro-8-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Product 1

HCID 576631608-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 9-chloro-8-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (1 equivalent), 10% palladium on charcoal (0.1 equivalents) and ammonium formate (10 equivalents) in methanol was heated at reflux for 2 hours. The mixture was allowed to cool, filtered through Celite® and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the organic phase washed with brine, dried (MgSO4), concentrated in vacuo and chromatographed on alumina, eluting with ethyl acetate, to give the desired compound as a colourless solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. filtrationfiltered through Celite®
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was partitioned between ethyl acetate and water
  7. washthe organic phase washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customchromatographed on alumina
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c072d528ffb543728f451a5bd2604f87
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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