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

HRID 325036Notes

Reaction equation

HRID 325036 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; 1M; 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-5390921ce5604507a4fc60d24bcec0d9
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

Loading…