5-(Methoxymethoxy)-6-nitroindane → 6-(Methoxymethoxy)indan-5-amine

HRID 1879404Notes

Reaction equation

HRID 1879404 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[CH2:10][CH2:9][CH2:8]2>CO.[C].[Pd]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11]([CH2:10][CH2:9][CH2:8]2)=[CH:12][C:13]=1[NH2:14]

Participants

4

Reactant 1

HCID 583984775-(Methoxymethoxy)-6-nitroindane

Product 1

HCID 583985166-(Methoxymethoxy)indan-5-amineYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4.20 g of 5-(methoxymethoxy)-6-nitroindane was dissolved in 42.0 mL of methanol, and 500 mg of 10% palladium carbon was added thereto, followed by stirring at room temperature for 6 hours under a hydrogen atmosphere. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 3.30 g of 6-(methoxymethoxy)indan-5-amine.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d57b10fc00504569989f55a64c0fc1dc
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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