4-Nitro-1-indanyl acetate → 4-Amino-1-indanyl acetate

HRID 325775Notes

Reaction equation

HRID 325775 reaction equation
[C:1]([O:4][CH:5]1[C:13]2[C:8](=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pt]=O>[C:1]([O:4][CH:5]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 131024574-Nitro-1-indanyl acetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 131024584-Amino-1-indanyl acetateYield 97.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A solution of 10.0 g (0.045 mole) of 4-nitro-1-indanyl acetate in 200 mL of ethanol was mixed with 0.1 g of platinum oxide in 20 mL of ethanol, and the mixture was contacted with hydrogen in a Parr hydrogenator. Upon complete uptake of hydrogen, the reaction mixture was allowed to stand for 16 hours. The platinum oxide was removed by filtration through diatomaceous earth, and the filter cake was washed with ethanol. The ethanol washings were combined with the filtrate, and the whole was concentrated under reduced pressure to give 8.4 g of 4-amino-1-indanyl acetate as an oil.

Workup

  1. customThe platinum oxide was removed by filtration through diatomaceous earth
  2. washthe filter cake was washed with ethanol
  3. concentrationthe whole was concentrated under reduced pressure

Sources & evidence

ORD record
ord-31bb8b8e52304bd48e4fd3f03e169948
Source dataset
uspto-grants-1984_04
Patent number
US04442296

Reaction notes

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