Cyclohexylamine → N-cyclohexyl-2-nitroaniline

HRID 220814Notes

Reaction equation

HRID 220814 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([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:11]1([NH:17][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 3101179N-cyclohexyl-2-nitroanilineYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-fluoronitrobenzene (5.0 g, 35.4 mmol), cyclohexylamine (4.5 ml, 39.0 mmol) and potassium carbon-ate (17.1 g, 124 mmol) in acetonitrile (100 ml) was heated at reflux for 2 days. The mixture was diluted with EtOAC, washed with water then brine, dried and partially concentrated in vacuo. The solid which precipitated was collected and washed with hexane to yield the title compound (6.7 g, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. additionThe mixture was diluted with EtOAC
  4. washwashed with water
  5. dry with materialbrine, dried
  6. concentrationpartially concentrated in vacuo
  7. customThe solid which precipitated
  8. customwas collected
  9. washwashed with hexane

Sources & evidence

ORD record
ord-96a5a38ccfaf44b2938cddca722aa335
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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