Water → 4-(Cyclohexylamino)-3-nitrobenzonitrile

HRID 1788585Notes

Reaction equation

HRID 1788585 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CN(C=O)C>[CH:13]1([NH:19][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 29852004-(Cyclohexylamino)-3-nitrobenzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g (5.48 mmol) 4-chloro-3-nitrobenzonitrile, Compound 126, and 1.14 g (11.51 mmol) of cyclohexylamine were heated overnight in 5 mL anhydrous DMF. After cooling to room temperature, the solution was added dropwise into 100 mL H2O stirring vigorously. The solids were collected by filtration and dried under vacuum yielding 1.34 g (100%) bright yellow solids which were used as such without analysis in the next step.

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-9f7d4870ad9a4abf8a731fdf8d91007d
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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