4,5-Diethoxy-3-fluorophthalonitrile → 5,6-diethoxy-7-fluoro-3H-isoindol-1-ylamine

HRID 1295950Notes

Reaction equation

HRID 1295950 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:17])=[C:6]([C:15]#[N:16])[C:7](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:8]#[N:9])[CH3:2]>C(OCC)(=O)C.C(O)C.CO.[Pt]=O>[CH2:1]([O:3][C:4]1[C:5]([F:17])=[C:6]2[C:7](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH2:8][N:9]=[C:15]2[NH2:16])[CH3:2]

Participants

4

Reactant 1

HCID 229298414,5-Diethoxy-3-fluorophthalonitrile

Product 1

HCID 99917775,6-diethoxy-7-fluoro-3H-isoindol-1-ylamineYield 20%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 18423184Ethyl acetate ethanol methanolSolvent

Procedure

After dissolving 4,5-diethoxy-3-fluorophthalonitrile (103 g) in ethyl acetate-ethanol-methanol (600 ml-600 ml-300 ml), platinum oxide (8 g) was added and the mixture was stirred at room temperature for 4 days under a hydrogen stream. The reaction mixture was filtered through celite, the organic layer was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (21 g) as yellow crystals.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite
  3. distillationthe organic layer was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3313e0d14f764dacad535d9e1fede670
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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