Acetic Acid → 4-Amino-6-fluoroisoindolin-1-one

HRID 1869323Notes

Reaction equation

HRID 1869323 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[CH2:14][N:15]=[N+]=[N-].C(O)(=O)C>C(O)C.[Pd]>[NH2:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:4]2[C:5]=1[CH2:14][NH:15][C:3]2=[O:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 860442842-(Azidomethyl)-5-fluoro-3-nitrobenzoic Acid Methyl Ester

Product 1

HCID 179850484-Amino-6-fluoroisoindolin-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.86 g (7.32 mmol) of 2-(azidomethyl)-5-fluoro-3-nitrobenzoic acid methyl ester is added in 46 ml of ethanol and 3.4 ml of glacial acetic acid and mixed with 256.6 mg of Pd/C. After stirring overnight at room temperature under hydrogen atmosphere, the catalyst is suctioned off via a glass-fiber filter, and the filtrate is evaporated to the dry state. The residue, 1.18 mg (97.5%) of the desired compound, is further incorporated in crude form.

Workup

  1. filtrationfilter
  2. customthe filtrate is evaporated to the dry state

Sources & evidence

ORD record
ord-3e55a77e528e4606a259b4b1e3967f63
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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