Cyclopropylamine → N-cyclopropyl-2-nitroaniline

HRID 1966979Notes

Reaction equation

HRID 1966979 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.F[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]>>[CH:1]1([NH:4][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-:14])=[O:13])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10487549N-cyclopropyl-2-nitroanilineYield 86.6%

Procedure

To cyclopropylamine (27.3 g, 33.1 mL, 0.48 mol, 2.25 equiv; [CAS RN 765-30-0]) was added dropwise 2-fluoronitrobenzene (30.0 g, 0.21 mol, 1.0 equiv; [CAS RN 1493-27-2]) over 1 hours at 30° C. and stirring of the reaction mixture continued at room temperature for 18 h. The reaction mixture was extracted from a saturated aqueous solution of sodium bicarbonate (500 mL) with ethyl acetate (three times 300 mL) and the combined organic phases were dried over magnesium sulfate. Purification by silica gel column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a mixture of n-heptane:ethyl acetate (9:1) afforded 32.4 g (86%) of the title compound as a yellow oil. MS (ISP): m/z=178.0 [M+H]+.

Workup

  1. extractionThe reaction mixture was extracted from a saturated aqueous solution of sodium bicarbonate (500 mL) with ethyl acetate (three times 300 mL)
  2. dry with materialthe combined organic phases were dried over magnesium sulfate
  3. customPurification by silica gel column chromatography
  4. washeluting with a mixture of n-heptane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-62ecad567037454db1ec5cc0c5b55fe0
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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