Ammonium formate → 5-Amino-2-ethyl-2,3-dihydro-1H-isoindol-1-one

HRID 1947630Notes

Reaction equation

HRID 1947630 reaction equation
[CH2:1]([N:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=2)[C:4]1=[O:15])[CH3:2].C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[NH2:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:15])[N:3]([CH2:1][CH3:2])[CH2:11]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67223854HCID 67223854, compound

Product 1

HCID 529112495-Amino-2-ethyl-2,3-dihydro-1H-isoindol-1-oneYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium/Carbon (10% wt) (63 mg, 0.30 mmol) was added to a stirred solution of 2-ethyl-5-nitro-2,3-dihydro-isoindol-1-one (634 mg, 3.06 mmol) and ammonium formate (949 mg, 15.31 mmol) in anhydrous DMF (12 ml) at room temperature. The resulting suspension was heated at reflux for 1 hr, then cooled and filtered through a pad of celite. The solvent was evaporated in vacuo and the crude residue purified by flash column chromatography (5% methanol in dichloromethane) to yield the title compound as a pale yellow oil (530 mg, 98%). HPLC retention time 0.95 min. Mass spectrum (ES+) m/z 177 (M+H).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 1 hr
  3. temperaturecooled
  4. filtrationfiltered through a pad of celite
  5. customThe solvent was evaporated in vacuo
  6. customthe crude residue purified by flash column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-299f0048b81743eda39b124a3739a2e3
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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