Cyclopropylamine → N-cyclopropyl-2-nitroaniline

HRID 1048656Notes

Reaction equation

HRID 1048656 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH:11]1([NH2:14])[CH2:13][CH2:12]1>C(O)C>[CH:11]1([NH:14][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10487549N-cyclopropyl-2-nitroanilineYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-fluoro-2-nitrobenzene (0.50 g, 3.5 mmol) in ethanol was added cyclopropyl amine (0.60 g, 10.5 mmol). The solution was heated to 80° C. overnight and concentrated. The residue was purified by biotage column chromatography to give N-cyclopropyl-2-nitroaniline (0.60 g)

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by biotage column chromatography

Sources & evidence

ORD record
ord-f55947f3bab349708f5c9b9c95740c9e
Source dataset
uspto-grants-2016_07
Patent number
US09381196B2

Reaction notes

Loading…