Cyclopentylamine → 5-bromo-N-cyclopentyl-2-nitroaniline

HRID 2264362Notes

Reaction equation

HRID 2264362 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]>C(O)CCC>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[C:8]([NH:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:13]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 123156462,4-Dibromo-1-nitrobenzene

Product 1

HCID 653413535-bromo-N-cyclopentyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Add cyclopentanamine (32 mL) to a solution of 2,4-dibromo-1-nitro-benzene (20 g) in 1-butanol (160 mL). Heat the mixture at 100° C. overnight. Remove the solvent under vacuum, add water and extract with EA. Wash the organic layer sequentially with an aqueous saturated solution of sodium bicarbonate and then water. Dry over magnesium sulfate and remove the solvent under vacuum to afford 22 g of the title compound. MS (ES+): m/z=286 (M+H)+.

Workup

  1. customRemove the solvent under vacuum
  2. additionadd water
  3. extractionextract with EA
  4. washWash the organic layer sequentially with an aqueous saturated solution of sodium bicarbonate
  5. dry with materialDry over magnesium sulfate
  6. customremove the solvent under vacuum

Sources & evidence

ORD record
ord-a3fe5ae5977840999ea2a400945b6900
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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