Cyclopropylamine → N-cyclopropyl-2-nitroaniline

HRID 2231242Notes

Reaction equation

HRID 2231242 reaction equation
Cl[C:2]1([CH:8]=[CH:7][CH:6]=[CH:5][CH:4]1[N+:9]([O-:11])=[O:10])[NH2:3].[CH:12]1(N)[CH2:14][CH2:13]1>C(OCC)(=O)C>[CH:12]1([NH:3][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N+:9]([O-:11])=[O:10])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 21286307HCID 21286307, compound

Product 1

HCID 10487549N-cyclopropyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Chloro-2-nitroaniline (13 g, 0.082 mole) and 17.15 ml of cyclopropylamine were heated together at reflux temperature for 24 hours, cooled and poured into ethyl acetate. The organic solution was washed with a saturated brine solution (3×100 ml), dried with magnesium sulfate and concentrated to dryness. The residue was chromatographed on silica gel using 60% hexane in chloroform to give 2.04 g of the desired intermediate.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. temperaturecooled
  3. washThe organic solution was washed with a saturated brine solution (3×100 ml)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on silica gel using 60% hexane in chloroform

Sources & evidence

ORD record
ord-4a257bddf2e14bf5beac81c4ac74384e
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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