Ethyl Acetate → Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 1791857Notes

Reaction equation

HRID 1791857 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-])=O)[CH:15]=2)=[CH:7][CH:6]=1)#[N:4].CCOC(C)=O>CCO.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:21][C:16]1[CH:15]=[C:14]([O:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)[CH:19]=[CH:18][C:17]=1[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 22033464[2-(4-Cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene

Product 1

HCID 22033532Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneYield 26%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

Sodium borohydride (0.127 g; 3.35 mmol) was added in portions to a cold suspension (ice:water temperature) of [2-(4-cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene (0.19 g; 0.67 mmol; from step (i) above) and aqueous copper sulfate (1.34 mL; 1 M; 1.34 mmol) in EtOH (5 mL) over five minutes. The temperature was allowed to rise to ambient and the stirring continued for 30 minutes. Addition of EtOAc (50 mL) and filtration through Celite afforded a clear solution that was washed with water, dried (K3CO3) and concentrated in vacuo. Flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 0.044 g (26%) of the sub-title compound as a white solid.

Workup

  1. customafforded a clear solution that
  2. washwas washed with water
  3. customdried (K3CO3)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97967a60623a4f7b94a70e73c45afd80
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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