5-nitro-1H-isochromen-1-one → HCID 55252553, compound

HRID 749217Notes

Reaction equation

HRID 749217 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][O:8][C:9]2=[O:14])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][O:8][C:9]2=[O:14]

Participants

4

Reactant 1

HCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 55252553HCID 55252553, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 250 mL round-bottom flask was charged with a solution of 5-nitro-1H-isochromen-1-one (3.0 g, 15.7 mmol) in absolute ethanol (60 mL) and 10% Pd/C (600 mg). The reaction vessel was evacuated and filled with hydrogen via balloon. The reaction suspension was stirred at room temperature in hydrogen atmosphere (via balloon) for 17 h. The resulting mixture was filtered and the solvent was removed on a rotary evaporator. After drying under reduced pressure, 2.40 g, (14.9 mmol, 95%) of 5-aminoisochroman-1-one were isolated as a white solid.

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with hydrogen via balloon
  3. filtrationThe resulting mixture was filtered
  4. customthe solvent was removed on a rotary evaporator
  5. customAfter drying under reduced pressure, 2.40 g

Sources & evidence

ORD record
ord-97fcfb01c2154e7b98b08e6822b688d5
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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