Cyclopropylamine → N-cyclopropyl-2-nitroaniline

HRID 1877386Notes

Reaction equation

HRID 1877386 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 h at 30° C. and stirring of the reaction mixture continued at rt for 18 h. The reaction mixture was extraction from a sat. solution of NaHCO3 (500 mL) with ethyl acetate (3×300 mL) and the combined organic phases dried over MgSO4. Purification by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a mixture of heptane/ethylacetate (9:1) afforded 32.4 g (86%) of the title compound as a yellow oil. MS (ISP): 178.0 [M+H]+.

Workup

  1. extractionextraction from a sat. solution of NaHCO3 (500 mL) with ethyl acetate (3×300 mL)
  2. dry with materialthe combined organic phases dried over MgSO4
  3. customPurification by silica column chromatography
  4. washeluting with a mixture of heptane/ethylacetate (9:1)

Sources & evidence

ORD record
ord-24d86879675f4f74889d7aced7c51b5c
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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