Ethanol → 4-Amino-6-fluoroisoindolin-1-one

HRID 2118067Notes

Reaction equation

HRID 2118067 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)C>[Pd].C(O)(=O)C>[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 702EthanolHCID 860442842-(Azidomethyl)-5-fluoro-3-nitrobenzoic Acid Methyl Ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.86 g (7.32 mmol) of 2-(azidomethyl)-5-fluoro-3-nitrobenzoic acid methyl ester is added into 46 ml of ethanol and 3.4 ml of glacial acetic acid, and it is mixed with 256.6 mg of Pd/C. After stirring overnight at room temperature under hydrogen atmosphere, the catalyst is suctioned off with 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 used in crude form.

Workup

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

Sources & evidence

ORD record
ord-38655646a433495a95da51c4a7cc65b3
Source dataset
uspto-grants-2008_10
Patent number
US07442794B2

Reaction notes

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