5,6-difluoro-2-hydroxyimino-3H-inden-1-one → 2-Amino-5,6-difluoroindan-1-one

HRID 2060883Notes

Reaction equation

HRID 2060883 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[C:6](=[N:13]O)[CH2:5]2>C(O)(=O)C.[Pd]>[NH2:13][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][C:10]([F:11])=[C:2]([F:1])[CH:3]=2)[C:7]1=[O:12]

Participants

4

Reactant 1

HCID 766113455,6-difluoro-2-hydroxyimino-3H-inden-1-one

Product 1

HCID 575859182-Amino-5,6-difluoroindan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5,6-Difluoroindan-1,2-dione 2-oxime (Preparation 77) (2.70 g, 13.7 mmol) was dissolved in acetic acid (70 mL) and 10% Palladium on carbon (717 mg) added. The reaction mixture was hydrogenated at 50 psi for 72 h, filtered through a pad of celite and washed with chloroform (100 mL). The resulting precipitate was collected by filtration and air dried to give the title compound: δH(DMSO-d6) 3.11 (1H, dd), 3.56 (1H, dd), 4.34 (1H, dd), 7.74-7.94 (2H, m), 8.75 (2H, bs).

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed with chloroform (100 mL)
  3. filtrationThe resulting precipitate was collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-d8a05766792d41bface76359afb003a1
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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