HCID 58453198, compound → 2-Bicyclopropyl-2-yl-phenylamine

HRID 2109528Notes

Reaction equation

HRID 2109528 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:12][CH:11]1[CH:13]1[CH2:15][CH2:14]1)([O-])=O.[H][H]>C(O)C.[Pt].[C]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:12][CH:11]1[CH:13]1[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 58453198HCID 58453198, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 167270602-Bicyclopropyl-2-yl-phenylamineYield 102.5%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 702EthanolSolvent

Procedure

In a hydrogenation reactor, 1 g of 2-(2-nitrophenyl)-bicyclopropane (4.9 mmol, trans:cis ratio: 4.1:1), dissolved in 20 ml of ethanol, is hydrogenated at ambient temperature using 0.1 g of 5% platinum-carbon catalyst. After 2.5 hours and after 101% of the amount of hydrogen theoretically required for the reduction has been taken up, the reaction is stopped. Following filtration of the reaction mixture, the solvent is removed by concentration by evaporation. 0.87 g of 2-(2-aminophenyl)-bicyclopropane (100% of theory) is obtained in the form of a brownish liquid (trans:cis ratio: 4.4:1).

Workup

  1. customis hydrogenated at ambient temperature
  2. filtrationfiltration of the reaction mixture
  3. customthe solvent is removed by concentration by evaporation

Sources & evidence

ORD record
ord-d7f25fc4fa9a456e8d230c94faae8e49
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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