Ethanol → 4-AMINOISOINDOLIN-1-ONE

HRID 1443121Notes

Reaction equation

HRID 1443121 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[CH2:13][N:14]=[N+]=[N-].C(O)C>[Pd].C(O)(=O)C>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[CH2:13][NH:14][C:3]2=[O:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 71417999Methyl 2-(azidomethyl)-3-nitrobenzoate

Product 1

HCID 98555134-AMINOISOINDOLIN-1-ONEYield 62.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1 g (4.2 mmol) of 2-(azidomethyl)-3-nitrobenzoic acid methyl ester is added to 10 ml of ethanol and 2 ml of glacial acetic acid and mixed with 148.5 mg of Pd/C. After stirring overnight at room temperature under a hydrogen atmosphere, the catalyst is suctioned off via a glass fiber filter, and the filtrate is evaporated to the dry state. The residue is chromatographed on a Flashmaster (mobile solvent). 391.5 mg (62.4%) of the desired compound is isolated.

Workup

  1. filtrationfilter
  2. customthe filtrate is evaporated to the dry state
  3. customThe residue is chromatographed on a Flashmaster (mobile solvent)

Sources & evidence

ORD record
ord-20b4dc958a1f4d8b8065e748b47494e6
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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